Heteroaryl azole herbicides

ABSTRACT

Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation                    
     and Q, W, X, Y, Z, and R 1  through R 8  are as defined in the disclosure. 
     Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a national stage entry under 35 U.S.C. 371 ofPCT/US98/04600, filed Mar. 9, 1998 which claims the benefit of U.S.Provisional Application Ser. No. 60/039,544 filed Mar. 11, 1997.

BACKGROUND OF THE INVENTION

This invention relates to certain heteroaryl azoles, their N-oxides,agriculturally suitable salts, compositions thereof, and methods oftheir use for controlling undesirable vegetation.

The control of undesired vegetation is extremely important in achievinghigh crop efficiency. Achievement of selective control of the growth ofweeds especially in such useful crops as rice, soybean, sugar beet, corn(maize), potato, wheat, barley, tomato and plantation crops, amongothers, is very desirable. Unchecked weed growth in such useful cropscan cause significant reduction in productivity and thereby result inincreased costs to the consumer. The control of undesired vegetation innoncrop areas is also important. Many products are commerciallyavailable for these purposes, but the need continues for new compoundswhich are more effective, less costly, less toxic, environmentally saferor have different modes of action.

WO 96/06096 discloses herbicidal substituted pyridines of the formula

wherein, inter alia,

R¹, R², and R³ are each independently hydrogen, alkyl, alkoxy, cyano,nitro or halogen;

Qa is optionally substituted phenyl, pyrazolyl or pyridyl;

Qb is azolyl;

X is O, S or NR⁴; and

R⁴ is H or alkyl.

The heteroaryl azoles of the present invention are not disclosed in thispublication.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula I including allgeometric and stereoisomers, N-oxides, and agriculturally suitable saltsthereof, as well as agricultural compositions containing them and amethod of their use for controlling undesirable vegetation:

W is N or CR⁹;

X, Y and Z are independently N, CH or CR⁹, provided that only one of X,Y and Z is CR⁹;

Q is O, S(O)_(n) or NR¹⁰;

R¹ and R² are independently H, halogen, cyano, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₂-C₄ alkoxyalkyl, C₃-C₅ dialkoxyalkyl, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₂-C₄ alkoxyalkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄alkenyloxy, C₃-C₄ alkynyloxy, S(O)_(n)R⁸, C₂-C₄ alkylthioalkyl, C₂-C₄alkylsulfonylalkyl, C₁-C₄ alkylamino or C₂-C₄ dialkylamino;

R³ is H, halogen, cyano, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄haloalkyl, C₂-C₄ alkoxyalkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄alkenyloxy, C₃-C₄ alkynyloxy or S(O)_(n)R⁸;

R⁴ is halogen, cyano, SF₅, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy or S(O)_(n)R⁸;

R⁵ is H, halogen, cyano, SF₅, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy or S(O)_(n)R⁸;

R⁶ is H, halogen, cyano, SF₅, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy or S(O)_(n)R⁸;

R⁷ is halogen, cyano, SF₅, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy or S(O)_(n)R⁸;

each R⁸ is independently C₁-C₄ alkyl or C₁-C₄ haloalkcyl;

each R⁹ is independently halogen, cyano, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkoxyalkyl, C₃-C₄ alkenyl, C₃-C₄alkynyl, C₃-C₄ alkenyloxy, C₃-C₄ alkynyloxy or S(O)_(n)R⁸;

R¹⁰ is H, C₁-C₄ alkyl or C₁-C₄ haloalkyl; and

each n is independently 0, 1 or 2.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. The term “1-2alkyl” indicates that one or two of the available positions for thatsubstituent may be alkyl which are independently selected. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy”includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy andthe different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl”denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” includeCH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.“Alkenyloxy” includes straight-chain or branched alkenyloxy moieties.Examples of “alkenyloxy” include H₂C═CHCH₂O, (CH₃)₂C═CHCH₂O,(CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O. “Alkynyloxy”includes straight-chain or branched alkynyloxy moieties. Examples of“alkynyloxy” include HC≡CCH₂O, CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O. “Alkylthio”includes branched or straight-chain alkylthio moieties such asmethylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylthioalkyl” denotes alkylthiosubstitution on alkyl. Examples of “alkylthioalkyl” include CH₃SCH₂,CH₃SCH₂CH₂, CH₃CH₂SCH₂, -CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂.“Alkylthioalkoxy” denotes alkylthio substitution on alkoxy.“Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group.Examples of “alkylsulfinyl” include CH₃S(O), CH₃CH₂S(O), CH₃CH₂CH₂S(O),(CH₃)₂CHS(O) and the different butylsulfinyl, pentylsulfinyl andhexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH₃S(O)₂,CH₃CH₂S(O)₂, CH₃CH₂CH₂S(O)₂, (CH₃)₂CHS(O)₂ and the differentbutylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. “Cyanoalkyl”denotes an alkyl group substituted with one cyano group. Examples of“cyanoalkyl” include NCCH₂, NCCH₂CH₂ and CH₃CH(CN)CH₂. “Alkylamino”,“dialkylamino”, “alkenylthio”, “alkenylsulfinyl”, “alkenylsulfonyl”,“alkynylthio”, “alkynylsulfinyl”, “alkynylsulfonyl”, and the like, aredefined analogously to the above examples.

One skilled in the art will appreciate that not all nitrogen containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

The term “halogen”, either alone or in compound words such as“haloalkyl”, includes fluorine, chlorine, bromine or iodine. The term“1-2 halogen” indicates that one or two of the available positions forthat substituent may be halogen which are independently selected.Further, when used in compound words such as “haloalkyl”, said alkyl maybe partially or fully substituted with halogen atoms which may be thesame or different. Examples of “haloalkyl” include F₃C, ClCH₂, CF₃CH₂and CF₃CCl₂. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”,“haloalkylthio”, and the like, are defined analogously to the term“haloalkyl”. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂ andCF₃CH₂CH═CHCH₂. Examples of “haloalkynyl” include HC≡CCHCl, CF₃C≡C,CCl₃C≡C and FCH₂C≡CCH₂. Examples of “haloalkoxy” include CF₃O, CCl₃CH₂O,HCF₂CH₂CH₂O and CF₃CH₂O. Examples of “haloalkylthio” include CCl₃S,CF₃S, CCl₃CH₂S and ClCH₂CH₂CH₂S. Examples of “haloalkylsulfinyl” includeCF₃S(O), CCl₃S(O), CF₃CH₂S(O) and CF₃CF₂S(O). Examples of“haloalkylsulfonyl” include CF₃S(O)₂, CCl₃S(O)₂, CF₃CH₂S(O)₂ andCF₃CF₂S(O)₂. Examples of “haloalkoxyalkoxy” include CF₃OCH₂O,ClCH₂CH₂OCH₂CH₂O, Cl₃CCH₂OCH₂O as well as branched alkyl derivatives.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 5. Forexample, C₁-C₃ alkylsulfonyl designates methylsulfonyl throughpropylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄alkoxyalkyl designates the various isomers of an alkyl group substitutedwith an alkoxy group containing a total of four carbon atoms, examplesincluding CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. Examples of “alkylcarbonyl”include C(O)CH₃, C(O)CH₂CH₂CH₃ and C(O)CH(CH₃)₂. Examples of“alkoxycarbonyl” include CH₃OC(═O), CH₃CH₂OC(═O), CH₃CH₂CH₂OC(═O),(CH₃)₂CHOC(═O) and the different butoxy- or pentoxycarbonyl isomers. Inthe above recitations, when a compound of Formula I is comprised of oneor more heterocyclic rings, all substituents are attached to these ringsthrough any available carbon or nitrogen by replacement of a hydrogen onsaid carbon or nitrogen.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents. Further, when the subscript indicates arange, e.g. (R)_(i-j), then the number of substituents may be selectedfrom the integers between i and j inclusive.

When a group contains a substituent which can be hydrogen, for exampleR¹⁰, then, when this substituent is taken as hydrogen, it is recognizedthat this is equivalent to said group being unsubstituted.

The compounds of this invention thus include compounds of Formula I,geometric and stereoisomers thereof, N-oxides thereof, andagriculturally suitable salts thereof. The compound of the invention canexist as one or more stereoisomers. The various stereoisomers includeenantiomers, diastereomers, atropisomers and geometric isomers. Oneskilled in the art will appreciate that one stereoisomer may be moreactive and/or may exhibit beneficial effects when enriched relative tothe other stereoisomer(s) or when separated from the otherstereoisomer(s). Additionally, the skilled artisan knows how toseparate, enrich, and/or to selectively prepare said stereoisomers. Thecompounds of the invention may be present as a mixture of stereoisomers,individual stereoisomers, or as an optically active form.

The salts of the compounds of the invention include acid-addition saltswith inorganic or organic acids such as hydrobromic, hydrochloric,nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic,malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic orvaleric acids. The salts of the compounds of the invention also includethose formed with organic bases (e.g., pyridine, ammonia, ortriethylamine) or inorganic bases (e.g., hydrides, hydroxides, orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium)when the compound contains an acidic group such as a carboxylic acid orphenol.

Preferred compounds of the invention for reasons of better activityand/or ease of synthesis are:

Preferred 1. Compounds of Formula I above, geometric and stereoisomersthereof, N-oxides thereof, and agriculturally-suitable salts thereof,wherein:

Q is 0;

R¹ and R² are independently H, C₁-C₄ alkyl or C₁-C₄ alkoxy; and

R³ is halogen, C₁-C₄ haloalkyl, C₁-C₄ haloalkoxy or C₁-C₄ haloalkylthio.

Preferred 2. Compounds of Preferred I wherein:

W is N;

Y is CR⁹; and

R⁵ is H.

Preferred 3. Compounds of Preferred 2 wherein:

R² is H; and

each R⁴ is independently halogen, C₁-C₄ haloalkyl, C₁-C₄ haloalkoxy orC₁-C₄ haloalkylthio.

Most preferred are compounds of Formula I above selected from the group:

(a)5-methyl-4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;

(b)4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;

(c)5-methyl-4-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]pyrimidine;

(d)5-methyl-2-[3-(Triluoromethyl)-1H-pyrazol-1-yl]4-[[6-(trifluoromethyl)-2-pyridinyl]oxy]pyrimidine;

(e)5-methyl-4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]pyrimidine;

(f)5-methyl-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]-4-[3-(trifluoromethyl)phenoxy]pyrimidine;

(g)5-ethyl4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;

(h)5-ethyl4-[3-(trifluoromethoxy)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;

(i)5-ethyl-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]4-[3-(trifluoromethyl)phenoxy)pyrimidine;and

(j) 5-ethyl-4-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]pyrimidine.

This invention also relates to herbicidal compositions comprisingherbicidally effective amounts of the compounds of the invention and atleast one of a surfactant, a solid diluent or a liquid diluent. Thepreferred compositions of the present invention are those which comprisethe above preferred compounds.

This invention also relates to a method for controlling undesiredvegetation comprising applying to the locus of the vegetationherbicidally effective amounts of the compounds of the invention (e.g.,as a composition described herein). The preferred methods of use arethose involving the above preferred compounds.

DETAILS OF THE INVENTION

The compounds of Formula I can be prepared by one or more of thefollowing methods and variations as described in Schemes 1-5. Thedefinitions of J, Q, W, X, Y, Z, R¹, R² and R³ in the compounds ofFormulae 1-4 below are as defined above in the Summary of the Invention.

Scheme 1 illustrates the preparation of compounds of Formula I whereincompounds of Formula 1 are allowed to react with compounds of Formula 2and a suitable base such as potassium carbonate, potassium hydroxide orsodium hydride in a solvent such as NN-dimethylformamide, acetonitrile,or tetrahydrofuran at temperatures ranging from 0° C. to 130° C.

Heterocycles of Formula 1 where L¹ is halogen can be prepared byreacting pyridines or pyrimidines of Formula 3 with azoles of Formula 4in the presence of a base such as potassium carbonate, potassiumhydroxide or sodium hydride in a solvent such as N,N-dimethylformamide,acetonitrile, or tetrahydrofuran at temperatures ranging from 0° C. to130° C. (Scheme 2). This condensation generally gives rise to mixturesof products of Formula 1 and 1a which can be separated by silica gelchromatography.

As shown in Scheme 3, heterocycles of Formula 1 where L¹ ismethylsulfonyl can be prepared from compounds of Formula 5 by oxidationwith m-chloroperoxybenzoic acid in a halogenated solvent such asdichloromethane or with Oxone® (potassium peroxymonosulfate) in analcohol solvent such as methanol at temperatures ranging from 0° C. to60° C. This type of oxidation reaction is well known in the art; forexample, see March, J. Advanced Organic Chemistry; John Wiley: New York,1992; 4^(th) edition, pp 1201-1203.

Scheme 4 illustrates the preparation of compounds of Formula 5 whereincompounds of Formula 6 (where L² is halogen) are allowed to react withcompounds of Formula 4 and a suitable base such as potassium carbonate,potassium hydroxide or sodium hydride in a solvent such asN,N-dimethylformamide or acetonitrile at temperatures ranging from 0° C.to 130° C.

Compounds of Formula 6 can be readily prepared by reaction of compoundsof Formula 3 with the sodium or potassium salt of methyl mercaptan in asolvent such as tetrahydrofuran or dioxane at temperatures ranging from0° C. to 80° C.

Dihaloheterocycles of Formula 3 can be obtained commercially or arereadily prepared by known methods in the art; for example, see Advancesin Heterocyclic Chemisty; Katritzky, A. R., Ed.; Academic Press: NewYork, 1993, volume 58, pp 301-305; Heterocyclic Compounds; Elderfield,R. C., Ed.; John Wiley: New York, 1957; volume 6, chapter 7, pp 265-270.

Compounds of Formula 4 can be obtained commercially or can be preparedby methods that are known in the art; for examples, see Elguero, J. etal. Organic Preparations and Procedures Int. (1995), 27, pp 33-74;Comprehensive Heterocyclic Chemistry; Potts, K., Ed.; Pergamon Press:New York, 1984; volume 5, chapters 4.04-4.13; Heterocyclic Compounds;Elderfield, R., Ed.; John Wiley: New York, 1957; volume 5, chapters 2and 4; and Baldwin, J. et al. J. Med. Chem. (1975), 18, pp 895-900;Evans, J. J. et al. U.S. Pat. No. 4,038,405 (1977).

As described for the oxidation above, compounds of Formula I wherein Qis S(O)_(n) and n is 1 or 2 can be prepared from compounds of Formula Iwherein Q is S(O)_(n) and n is 0 by treatment with an oxidizing reagentsuch as m-chloroperoxybenzoic acid or Oxone® (potassiumperoxymonosulfate).

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula I may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula I. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula I.

One skilled in the art will also recognize that compounds of Formula Iand the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. Percentages are by weight except for chromatographic solventmixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; s=singlet, d=doublet, t=triplet, q=quartet,m=multiplet, dd=doublet of doublets, dt=doublet of triplets, br s=broadsinglet.

EXAMPLE 1

Step A: Preparation of2-bromo-6-[3-(trifluoromethyl)-1H-prazol-1-yl]pyridine

A mixture of 2,6-dibromopyridine (3.5 g, 22 mmol),3-(trifluoromethyl)-1H-pyrazole 2.0 g, 15 mmol) and potassium carbonate(4.0 g, 29 mmol) was heated in 25 mL of N,N-dimethylformamide at 90° C.for 3 h. The reaction mixture was partitioned between ethyl acetate andwater. The separated organic layer was washed twice with brine, driedover magnesium sulfate, and evaporated under reduced pressure to give anoily residue which was purified by flash chromatography on silica gel(50:1 to 20:1 hexane/ethyl acetate) to yield 1.2 g of the title compoundof Step A as a white solid melting at 55-56° C. ¹H NMR (CDCl₃): δ 6.73(d, 1H), 7.45 (d, 1H), 7.71 (t, 1H), 7.97 (d, 1H), 8.60 (d, 1H).

Step B: Preparation of2-[3-(trifluoromethyl)phenoxyl-6-f3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine

A mixture of the title compound of Step A (0.9 g, 3.1 mmol),3-trifluoromethylphenol (0.7 g, 4.3 mmol) and potassium carbonate (0.9g, 6.5 mmol) was heated in 15 mL of N,N-dimethylformamide at 110-120° C.for 7 h. The reaction mixture was then partitioned between ethyl acetateand water. The separated organic layer was washed with water and brine,dried over magnesium sulfate, and evaporated under reduced pressure togive an oily residue. Purification by flash chromatography on silica gel(40:1 hexane/ethyl acetate) afforded 1.1 g of the title compound of StepB, a compound of this invention, as a white solid melting at 53-55° C.¹H NMR (CDCl₃): δ 6.60 (d, 1H), 6.92 (d, 1H), 7.36 (d, 1H), 7.43-7.60(m, 3H), 7.73 (d, 1H), 7.88 (t, 1H), 8.12 (d, 1H).

EXAMPLE 2

Step A: Preparation of4-chloro-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine

A mixture of 2,4-dichloropyrimidine (3.0.g, 20 mmol),3-(trifluoromethyl)-1H-pyrazole (2.5 g, 18 mmol) and potassium carbonate(5.0 g, 36 mmol) was stirred in 25 mL of N,N-dimethylformamide at roomtemperature overnight. The reaction mixture was partitioned betweenethyl acetate and water. The separated organic layer was washed twicewith brine, dried over magnesium sulfate, and evaporated under reducedpressure to a crude solid. Flash chromatography on silica gel (50:1 to25:1 to 110:1 to 3:1 hexane/ethyl acetate) afforded 0.5 g of the titlecompound of Step A as a solid melting at 123-125° C. and 2.3 g of theisomer 2-chloro-6-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine as asolid melting at 111-112° C. ¹H NMR (CDCl₃): δ 6.77 (d, 1H), 7.35 (d,1H), 8.65 (d, 1H), 8.70 (d, 1H).

Step B: Preparation of4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine

A mixture of the title compound of Step A (0.5 g, 2 mmol),3-trifluoromethylphenol (0.4 g, 2.5 mmol) and potassium carbonate (0.5g, 3.6 mmol) was stirred in 10 mL of N,N-dimethylformamide at roomtemperature overnight. The reaction mixture was partitioned betweenethyl acetate and water. The separated organic layer was washed twicewith brine, dried over magnesium sulfate, and evaporated under reducedpressure to give an oily residue. Flash chromatography on silica gel(5:1 to 3:1 hexane/ethyl acetate) afforded 0.3 g of the title compoundof Step B, a compound of this invention, as a white solid, melting at72-73° C. ¹H NMR (CDCl₃): δ 6.65 (d, 1H), 6.91 (d, 1H), 7.40-7.65 (m,4H), 8.22 (d, 1H), 8.71 (d, 1H).

EXAMPLE 3

Step A: Preparation of 2-chloro-5-methyl-4-methylthio]pyrimidine

To a solution of 2,4-dichloro-5-methylpyrimidine (10.0 g, 61 mmol)stirring in 200 mL of tetrahydrofuiran was added sodium thiomethoxide(5.0 g, 71 mmol) and the mixture stirred at room temperature overnight.The reaction mixture was partitioned between 200 mL of ethyl acetate and200 mL of water. The separated organic layer was washed twice with waterand brine, dried over magnesium sulfate, and evaporated under reducedpressure to give a white solid which was suspended in a minimal amountof hexanes and filtered. Additional solid was filtered from the filtrateseveral times and all of the crops were combined to give 9.3 g of thetitle compound of Step A as a solid melting at 75-77° C. ¹H NMR (CDCl₃):δ 8.02 (s, 1H), 2.60 (s, 3H) 2.17 (s, 3H).

Step B: Preparation of5-methyl-4-methylthio-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine

A mixture of 2-chloro-5-methyl-4-methylthiopyrimidine (2.5 g, 14 mmol),3-(trifluoromethyl)-1H-pyrazole (2.3 g, 2.5 mmol) and potassiumcarbonate (4.8 g, 35 mmol) in 25 mL of N,N-dimethylformamide was heatedat 70° C. with stirring for 5 hours. The reaction mixture was thenpartitioned between ethyl acetate and water. The organic layer wasseparated, washed twice with water and brine and dried over magnesiumsulfate. The solvent was removed under reduced pressure to provide awhite solid which was suspended in hexane and filtered to provide 2.4 gof the title compound of Step B as a solid melting at 126-127° C. ¹H NMR(CDCl₃): δ 8.63 (d, 1H), 8.24 (s, 1H), 6.73 (d, 1H), 2.68 (s, 3H) 2.25(s, 3H).

Step C: Preparation of5-methyl-4-(methylsulfonyl)-2-[3-(trifluoromethyl)-1H-13pyrazol-1-yl]pyrimidine

To a solution of5-methyl-4-methylthio-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine(2.4 g, 9 mmol) stirred in 40 mL of dichloromethane was addedm-chloroperoxybenzoic acid (5 g, 57-86%). A solid gradually precipitatedand the white slurry stirred overnight at room temperature. The reactionmixture was filtered and the filtrate evaporated under reduced pressureto give a residue which was dissolved in 130 mL of diethyl ether. Afterwashing twice with aqueous sodium bisulfite, three times with aqueoussodium bicarbonate and brine, the organic layer was dried over magnesiumsulfate. The solvent was removed under reduced pressure to give a whitesolid which was suspended in hexane and filtered to give 2.4 g of thetitle compound of Step C as a solid melting at 129-131° C. ¹H NMR(CDCl₃): δ 8.87 (s, 1H), 8.57 (d, 1H), 6.79 (d, 1H), 3.49 (s, 3H) 2.73(s, 3H).

Step D: Preparation of5-methyl-4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-1)pyrazol-1-yl]pyrimidine

A mixture of5-methyl-4-methylsulfonyl-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine(0.3 g, 1 mmol), 3-trifluoromethylphenol (0.2 mL, 1.3 mmol) andpotassium carbonate (0.3 g, 2 mmol) in 10 mL of N,N-dimethylformamidewas stirred at room temperature overnight. The reaction mixture waspartitioned between ethyl acetate and water. The organic layer wasseparated and washed with water, saturated aqueous sodium bicarbonateand brine. After drying over magnesium sulfate, the solvent was removedunder reduced pressure to give an oily residue. Purification by flashchromatography on silica gel (5:1 followed by 3:1 hexane/ethyl acetate)afforded 150 mg of the title compound of Step D, a compound of thisinvention, as a white solid melting at 113-115° C. ¹H NMR (CDCl₃): δ8.53 (s, 1H), 8.07 (d, 1H), 7.65-7.58 (m, 2H), 7.57 (s, 1H), 7.47-7.40(m, 1H), 6.61 (d, 1H), 2.48 (s, 3H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 5 can be prepared.

TABLE 1

W R¹ R³ R⁴ W R¹ R³ R⁴ wherein X is N and Y and Z are CH CH H CF₃ 3-CF₃ NCH₂CH₃ CF₃ 3-CF₃ CH H CF₃ 3-OCF₃ N CH₂CH₃ CF₃ 3-OCF₃ CH H CF₃ 3-SCF₃ NCH₂CH₃ CF₃ 3-SCF₃ CH H CF₃ 3-OCHF₂ N CH₂CH₃ CF₃ 3-OCHF₂ CH H CF₃ 3-SCHF₂N CH₂CH₃ CF₃ 3-SCHF₂ CH H CF₃ 3-Cl N CH₂CH₃ CF₃ 3-Cl CH H OCHF₂ 3-CF₃ NCH₂CH₃ OCHF₂ 3-CF₃ CH H OCHF₂ 3-OCF₃ N CH₂CH₃ OCHF₂ 3-OCF₃ CH H OCHF₂3-SCF₃ N CH₂CH₃ OCHF₂ 3-SCF₃ CH H OCHF₂ 3-OCHF₂ N CH₂CH₃ OCHF₂ 3-OCHF₂CH H OCHF₂ 3-SCHF₂ N CH₂CH₃ OCHF₂ 3-SCHF₂ CH H OCHF₂ 3-Cl N CH₂CH₃ OCHF₂3-Cl CH H SCHF₂ 3-CF₃ N CH₂CH₃ SCHF₂ 3-CF₃ CH H SCHF₂ 3-OCF₃ N CH₂CH₃SCHF₂ 3-OCF₃ CH H SCHF₂ 3-SCF₃ N CH₂CH₃ SCHF₂ 3-SCF₃ CH H SCHF₂ 3-OCHF₂N CH₂CH₃ SCHF₂ 3-OCHF₂ CH H SCHF₂ 3-SCHF₂ N CH₂CH₃ SCHF₂ 3-SCHF₂ CH HSCHF₂ 3-Cl N CH₂CH₃ SCHF₂ 3-Cl CH H OCF₃ 3-CF₃ N CH₂CH₃ OCF₃ 3-CF₃ CH HOCF₃ 3-OCF₃ N CH₂CH₃ OCF₃ 3-OCF₃ CH H OCF₃ 3-SCF₃ N CH₂CH₃ OCF₃ 3-SCF₃CH H OCF₃ 3-OCHF₂ N CH₂CH₃ OCF₃ 3-OCHF₂ CH H OCF₃ 3-SCHF₂ N CH₂CH₃ OCF₃3-SCHF₂ CH H OCF₃ 3-Cl N CH₂CH₃ OCF₃ 3-Cl CH H SCF₃ 3-CF₃ N CH₂CH₃ SCF₃3-CF₃ CH H SCF₃ 3-OCF₃ N CH₂CH₃ SCF₃ 3-OCF₃ CH H SCF₃ 3-SCF₃ N CH₂CH₃SCF₃ 3-SCF₃ CH H SCF₃ 3-OCHF₂ N CH₂CH₃ SCF₃ 3-OCHF₂ CH H SCF₃ 3-SCHF₂ NCH₂CH₃ SCF₃ 3-SCHF₂ CH H SCF₃ 3-Cl N CH₂CH₃ SCF₃ 3-Cl CH H Cl 3-CF₃ NCH₂CH₃ Cl 3-CF₃ CH H Cl 3-OCF₃ N CH₂CH₃ Cl 3-OCF₃ CH H Cl 3-SCF₃ NCH₂CH₃ Cl 3-SCF₃ CH H Cl 3-OCHF₂ N CH₂CH₃ Cl 3-OCHF₂ CH H Cl 3-SCHF₂ NCH₂CH₃ Cl 3-SCHF₂ CH H Cl 3-Cl N CH₂CH₃ Cl 3-Cl CH CH₃ CF₃ 3-CF₃ N CH₃CF₃ 3-CF₃ CH CH₃ CF₃ 3-OCF₃ N CH₃ CF₃ 3-OCF₃ CH CH₃ CF₃ 3-SCF₃ N CH₃ CF₃3-SCF₃ CH CH₃ CF₃ 3-OCHF₂ N CH₃ CF₃ 3-OCHF₂ CH CH₃ CF₃ 3-SCHF₂ N CH₃ CF₃3-SCHF₂ CH CH₃ CF₃ 3-Cl N CH₃ CF₃ 3-Cl CH CH₃ OCHF₂ 3-CF₃ N CH₃ OCHF₂3-CF₃ CH CH₃ OCHF₂ 3-OCF₃ N CH₃ OCHF₂ 3-OCF₃ CH CH₃ OCHF₂ 3-SCF₃ N CH₃OCHF₂ 3-SCF₃ CH CH₃ OCHF₂ 3-OCHF₂ N CH₃ OCHF₂ 3-OCHF₂ CH CH₃ OCHF₂3-SCHF₂ N CH₃ OCHF₂ 3-SCHF₂ CH CH₃ OCHF₂ 3-Cl N CH₃ OCHF₂ 3-Cl CH CH₃SCHF₂ 3-CF₃ N CH₃ SCHF₂ 3-CF₃ CH CH₃ SCHF₂ 3-OCF₃ N CH₃ SCHF₂ 3-OCF₃ CHCH₃ SCHF₂ 3-SCF₃ N CH₃ SCHF₂ 3-SCF₃ CH CH₃ SCHF₂ 3-OCHF₂ N CH₃ SCHF₂3-OCHF₂ CH CH₃ SCHF₂ 3-SCHF₂ N CH₃ SCHF₂ 3-SCHF₂ CH CH₃ SCHF₂ 3-Cl N CH₃SCHF₂ 3-Cl CH CH₃ OCF₃ 3-CF₃ N CH₃ OCF₃ 3-CF₃ CH CH₃ OCF₃ 3-OCF₃ N CH₃OCF₃ 3-OCF₃ CH CH₃ OCF₃ 3-SCF₃ N CH₃ OCF₃ 3-SCF₃ CH CH₃ OCF₃ 3-OCHF₂ NCH₃ OCF₃ 3-OCHF₂ CH CH₃ OCF₃ 3-SCHF₂ N CH₃ OCF₃ 3-SCHF₂ CH CH₃ OCF₃ 3-ClN CH₃ OCF₃ 3-Cl CH CH₃ SCF₃ 3-CF₃ N CH₃ SCF₃ 3-CF₃ CH CH₃ SCF₃ 3-OCF₃ NCH₃ SCF₃ 3-OCF₃ CH CH₃ SCF₃ 3-SCF₃ N CH₃ SCF₃ 3-SCF₃ CH CH₃ SCF₃ 3-OCHF₂N CH₃ SCF₃ 3-OCHF₂ CH CH₃ SCF₃ 3-SCHF₂ N CH₃ SCF₃ 3-SCHF₂ CH CH₃ SCF₃3-Cl N CH₃ SCF₃ 3-Cl CH CH₃ Cl 3-CF₃ N CH₃ Cl 3-CF₃ CH CH₃ Cl 3-OCF₃ NCH₃ Cl 3-OCF₃ CH CH₃ Cl 3-SCF₃ N CH₃ Cl 3-SCF₃ CH CH₃ Cl 3-OCHF₂ N CH₃Cl 3-OCHF₂ CH CH₃ Cl 3-SCHF₂ N CH₃ Cl 3-SCHF₂ CH CH₃ Cl 3-Cl N CH₃ Cl3-Cl CH OCH₃ CF₃ 3-CF₃ N OCH₃ CF₃ 3-CF₃ CH OCH₃ CF₃ 3-OCF₃ N OCH₃ CF₃3-OCF₃ CH OCH₃ CF₃ 3-SCF₃ N OCH₃ CF₃ 3-SCF₃ CH OCH₃ CF₃ 3-OCHF₂ N 6CH₃CF₃ 3-OCHF₂ CH OCH₃ CF₃ 3-SCHF₂ N OCH₃ CF₃ 3-SCHF₂ CH OCH₃ CF₃ 3-Cl NOCH₃ CF₃ 3-Cl CH OCH₃ OCHF₂ 3-CF₃ N OCH₃ OCHF₂ 3-CF₃ CH OCH₃ OCHF₂3-OCF₃ N OCH₃ OCHF₂ 3-OCF₃ CH OCH₃ OCHF₂ 3-SCF₃ N OCH₃ OCHF₂ 3-SCF₃ CHOCH₃ OCHF₂ 3-OCHF₂ N OCH₃ OCHF₂ 3-OCHF₂ CH OCH₃ OCHF₂ 3-SCHF₂ N OCH₃OCHF₂ 3-SCHF₂ CH OCH₃ OCHF₂ 3-Cl N OCH₃ OCHF₂ 3-Cl CH OCH₃ SCHF₂ 3-CF₃ NOCH₃ SCHF₂ 3-CF₃ CH OCH₃ SCHF₂ 3-OCF₃ N OCH₃ SCHF₂ 3-OCF₃ CH OCH₃ SCHF₂3-SCF₃ N OCH₃ SCHF₂ 3-SCF₃ CH OCH₃ SCHF₂ 3-OCHF₂ N OCH₃ SCHF₂ 3-OCHF₂ CHOCH₃ SCHF₂ 3-SCHF₂ N OCH₃ SCHF₂ 3-SCHF₂ CH OCH₃ SCHF₂ 3-Cl N OCH₃ SCHF₂3-Cl CH OCH₃ OCF₃ 3-CF₃ N OCH₃ OCF₃ 3-CF₃ CH OCH₃ OCF₃ 3-OCF₃ N OCH₃OCF₃ 3-OCF₃ CH OCH₃ OCF₃ 3-SCF₃ N OCH₃ OCF₃ 3-SCF₃ CH OCH₃ OCF₃ 3-OCHF₂N OCH₃ OCF₃ 3-OCHF₂ CH OCH₃ OCF₃ 3-SCHF₂ N OCH₃ OCF₃ 3-SCHF₂ CH OCH₃OCF₃ 3-Cl N OCH₃ OCF₃ 3-Cl CH OCH₃ SCF₃ 3-CF₃ N OCH₃ SCF₃ 3-CF₃ CH OCH₃SCF₃ 3-OCF₃ N OCH₃ SCF₃ 3-OCF₃ CH OCH₃ SCF₃ 3-SCF₃ N OCH₃ SCF₃ 3-SCF₃ CHOCH₃ SCF₃ 3-OCHF₂ N OCH₃ SCF₃ 3-OCHF₂ CH OCH₃ SCF₃ 3-SCHF₂ N OCH₃ SCF₃3-SCHF₂ CH OCH₃ SCF₃ 3-Cl N OCH₃ SCF₃ 3-Cl CH OCH₃ Cl 3-CF₃ N OCH₃ Cl3-CF₃ CH OCH₃ Cl 3-OCF₃ N OCH₃ Cl 3-OCF₃ CH OCH₃ Cl 3-SCF₃ N OCH₃ Cl3-SCF₃ CH OCH₃ Cl 3-OCHF₂ N OCH₃ Cl 3-OCHF₂ CH OCH₃ Cl 3-SCHF₂ N OCH₃ Cl3-SCHF₂ CH OCH₃ Cl 3-Cl N OCH₃ Cl 3-Cl wherein Z is N and X and Y are CHCH H CF₃ 3-CF₃ N CH₂CH₃ CF₃ 3-CF₃ CH H CF₃ 3-OCF₃ N CH₂CH₃ CF₃ 3-OCF₃ CHH CF₃ 3-SCF₃ N CH₂CH₃ CF₃ 3-SCF₃ CH H CF₃ 3-OCHF₂ N CH₂CH₃ CF₃ 3-OCHF₂CH H CF₃ 3-SCHF₂ N CH₂CH₃ CF₃ 3-SCHF₂ CH H CF₃ 3-Cl N CH₂CH₃ CF₃ 3-Cl CHH OCHF₂ 3-CF₃ N CH₂CH₃ OCHF₂ 3-CF₃ CH H OCHF₂ 3-OCF₃ N CH₂CH₃ OCHF₂3-OCF₃ CH H OCHF₂ 3-SCF₃ N CH₂CH₃ OCHF₂ 3-SCF₃ CH H OCHF₂ 3-OCHFZ NCH₂CH₃ OCHF₂ 3-OCHF₂ CH H OCHF₂ 3-SCHF₂ N CH₂CH₃ OCHF₂ 3-SCHF₂ CH HOCHF₂ 3-Cl N CH₂CH₃ OCHF₂ 3-Cl CH H SCHF₂ 3-CF₃ N CH₂CH₃ SCHF₂ 3-CF₃ CHH SCHF₂ 3-OCF₃ N CH₂CH₃ SCHF₂ 3-OCF₃ CH H SCHF₂ 3-SCF₃ N CH₂CH₃ S&HF₂3-SCF₃ CH H SCHF₂ 3-OCHF₂ N CH₂CH₃ SCHF₂ 3-OCHF₂ CH H SCHF₂ 3-SCHF₂ NCH₂CH₃ SCHF₂ 3-SCHF₂ CH H SCHF₂ 3-Cl N CH₂CH₃ SCHF₂ 3-Cl CH H OCF₃ 3-CF₃N CH₂CH₃ OCF₃ 3-CF₃ CH H OCF₃ 3-OCF₃ N CH₂CH₃ OCF₃ 3-OCF₃ CH H OCF₃3-SCF₃ N CH₂CH₃ OCF₃ 3-SCF₃ CH H OCF₃ 3-OCHF₂ N CH₂CH₃ OCF₃ 3-OCHF₂ CH HOCF₃ 3-SCHF₂ N CH₂CH₃ OCF₃ 3-SCHF₂ CH H OCF₃ 3-Cl N CH₂CH₃ OCF₃ 3-Cl CHH SCF₃ 3-CF₃ N CH₂CH₃ SCF₃ 3-CF₃ CH H SCF₃ 3-OCF₃ N CH₂CH₃ SCF₃ 3-OCF₃CH H SCF₃ 3-SCF₃ N CH₂CH₃ SCF₃ 3-SCF₃ CH H SCF₃ 3-OCHF₂ N CH₂CH₃ SCF₃3-OCHF₂ CH H SCF₃ 3-SCHF₂ N CH₂CH₃ SCF₃ 3-SCHF₂ CH H SCF₃ 3-Cl N CH₂CH₃SCF₃ 3-Cl CH H Cl 3-CF₃ N CH₂CH₃ Cl 3-CF₃ CH H Cl 3-OCF₃ N CH₂CH₃ Cl3-OCF₃ CH H Cl 3-SCF₃ N CH₂CH₃ Cl 3-SCF₃ CH H Cl 3-OCHF₂ N CH₂CH₃ Cl3-OCHF₂ CH H Cl 3-SCHF₂ N CH₂CH₃ Cl 3-SCHF₂ CH H Cl 3-Cl N CH₂CH₃ Cl3-Cl CH CH₃ CF₃ 3-CF₃ N CH₃ CF₃ 3-CF₃ CH CH₃ CF₃ 3-OCF₃ N CH₃ CF₃ 3-OCF₃CH CH₃ CF₃ 3-SCF₃ N CH₃ CF₃ 3-SCF₃ CH CH₃ CF₃ 3-OCHF₂ N CH₃ CF₃ 3-OCHF₂CH CH₃ CF₃ 3-SCHF₂ N CH₃ CF₃ 3-SCHF₂ CH CH₃ CF₃ 3-Cl N CH₃ CF₃ 3-Cl CHCH₃ OCHF₂ 3-CF₃ N CH₃ OCHF₂ 3-CF₃ CH CH₃ OCHF₂ 3-OCF₃ N CH₃ OCHF₂ 3-OCF₃CH CH₃ OCHF₂ 3-SCF₃ N CH₃ OCHF₂ 3-SCF₃ CH CH₃ OCHF₂ 3-OCHF₂ N CH₃ OCHF₂3-OCHF₂ CH CH₃ OCHF₂ 3-SCHF₂ N CH₃ CCHF₂ 3-SCHF₂ CH CH₃ OCHF₂ 3-Cl N CH₃OCHF₂ 3-Cl CH CH₃ SCHF₂ 3-CF₃ N CH₃ SCHF₂ 3-CF₃ CH CH₃ SCHF₂ 3-OCF₃ NCH₃ SCHF₂ 3-OCF₃ CH CH₃ SCHF₂ 3-SCF₃ N CH₃ SCHF₂ 3-SCF₃ CH CH₃ SCHF₂3-OCHF₂ N CH₃ SCHF₂ 3-OCHF₂ CH CH₃ SCHF₂ 3-SCHF₂ N CH₃ SCHF₂ 3-SCHF₂ CHCH₃ SCHF₂ 3-Cl N CH₃ SCHF₂ 3-Cl CH CH₃ OCF₃ 3-CF₃ N CH₃ OCF₃ 3-CF₃ CHCH₃ OCF₃ 3-OCF₃ N CH₃ OCF₃ 3-OCF₃ CH CH₃ OCF₃ 3-SCF₃ N CH₃ OCF₃ 3-SCF₃CH CH₃ OCF₃ 3-OCHF₂ N CH₃ OCF₃ 3-OCHF₂ CH CH₃ OCF₃ 3-SCHF₂ N CH₃ OCF₃3-SCHF₂ CH CH₃ OCF₃ 3-Cl N CH₃ OCF₃ 3-Cl CH CH₃ SCF₃ 3-CF₃ N CH₃ SCF₃3-CF₃ CH CH₃ SCF₃ 3-OCF₃ N CH₃ SCF₃ 3-OCF₃ CH CH₃ SCF₃ 3-SCF₃ N CH₃ SCF₃3-SCF₃ CH CH₃ SCF₃ 3-OCHF₂ N CFI3 SCF₃ 3-OCHF₂ CH CH₃ SCF₃ 3-SCHF₂ N CH₃SCF₃ 3-SCHF₂ CH CH₃ SCF₃ 3-Cl N CH₃ SCF₃ 3-Cl CH CH₃ Cl 3-CF₃ N CH₃ Cl3-CF₃ CH CH₃ Cl 3-OCF₃ N CH₃ Cl 3-OCF₃ CH CH₃ Cl 3-SCF₃ N CH₃ Cl 3-SCF₃CH CH₃ Cl 3-OCHF₂ N CH₃ Cl 3-OCHF₂ CH CH₃ Cl 3-SCHF₂ N CH₃ Cl 3-SCHF₂ CHCH₃ Cl 3-Cl N CH₃ Cl 3-Cl CH OCH₃ CF₃ 3-CF₃ N OCH₃ CF₃ 3-CF₃ CH OCH₃ CF₃3-OCF₃ N OCH₃ CF₃ 3-OCF₃ CH OCH₃ CF₃ 3-SCF₃ N OCH₃ CF₃ 3-SCF₃ CH OCH₃CF₃ 3-OCHF₂ N OCH₃ CF₃ 3-OCHF₂ CH OCH₃ CF₃ 3-SCHF₂ N OCH₃ CF₃ 3-SCHF₂ CHOCH₃ CF₃ 3-Cl N 09H₃ CF₃ 3-Cl CH OCH₃ OCHF₂ 3-CF₃ N OCH₃ OCHF₂ 3-CF₃ CHOCH₃ OCHF₂ 3-OCF₃ N OCH₃ OCHF₂ 3-OCF₃ CH OCH₃ OCHF₂ 3-SCF₃ N OCH₃ OCHF₂3-SCF₃ CH OCH₃ OCHF₂ 3-OCHF₂ N OCH₃ OCHF₂ 3-OCHF₂ CH OCH₃ OCHF₂ 3-SCHF₂N OCH₃ OCHF₂ 3-SCHF₂ CH OCH₃ OCHF₂ 3-Cl N OCH₃ OCHF₂ 3-Cl CH OCH₃ SCHF₂3-CF₃ N OCH₃ SCHF₂ 3-CF₃ CH OCH₃ SCHF₂ 3-OCF₃ N OCH₃ SCHF₂ 3-OCF₃ CHOCH₃ SCHF₂ 3-SCF₃ N OCH₃ SCHF₂ 3-SCF₃ CH OCH₃ SCHF₂ 3-OCHF₂ N OCH₃ SCHF₂3-OCHF₂ CH OCH₃ SCHF₂ 3-SCHF₂ N OCH₃ SCHF₂ 3-SCHF₂ CH OCH₃ SCHF₂ 3-Cl NOCH₃ SCHF₂ 3-Cl CH OCH₃ OCF₃ 3-CF₃ N OCH₃ OCF₃ 3-CF₃ CH OCH₃ OCF₃ 3-OCF₃N OCH₃ OCF₃ 3-OCF₃ CH OCH₃ OCF₃ 3-SCF₃ N OCH₃ OCF₃ 3-SCF₃ CH OCH₃ OCF₃3-OCHF₂ N OCH₃ OCF₃ 3-OCHF₂ CH OCH₃ OCF₃ 3-SCHF₂ N OCH₃ OCF₃ 3-SCHF₂ CHOCH₃ OCF₃ 3-Cl N OCH₃ OCF₃ 3-Cl CH OCH₃ SCF₃ 3-CF₃ N OCH₃ SCF₃ 3-CF₃ CHOCH₃ SCF₃ 3-OCF₃ N OCH₃ SCF₃ 3-OCF₃ CH OCH₃ SCF₃ 3-SCF₃ N OCH₃ SCF₃3-SCF₃ CH OCH₃ SCF₃ 3-OCHF₂ N OCH₃ SCF₃ 3-OCHF₂ CH OCH₃ SCF₃ 3-SCHF₂ NOCH₃ SCF₃ 3-SCHF₂ CH OCH₃ SCF₃ 3-Cl N OCH₃ SCF₃ 3-Cl CH OCH₃ Cl 3-CF₃ NOCH₃ Cl 3-CF₃ CH OCH₃ Cl 3-OCF₃ N OCH₃ Cl 3-OCF₃ CH OCH₃ Cl 3-SCF₃ NOCH₃ Cl 3-SCF₃ CH OCH₃ Cl 3-OCHF₂ N OCH₃ Cl 3-OCHF₂ CH OCH₃ Cl 3-SCHF₂ NOCH₃ Cl 3-SCHF₂ CH OCH₃ Cl 3-Cl N OCH₃ Cl 3-Cl

TABLE 2

W R¹ R³ R⁴ W R¹ R³ R⁴ wherein X is N and Y and Z are CH CH H CF₃ 6-CF₃ NCH₂CH₃ CF₃ 6-CF₃ CH H CF₃ 6-OCF₃ N CH₂CH₃ CF₃ 6-OCF₃ CH H OCHF₂ 6-CF₃ NCH₂CH₃ OCHF₂ 6-CF₃ CH H OCHF₂ 6-OCF₃ N CH₂CH₃ OCHF₂ 6-OCF₃ CH H SCHF₂6-CF₃ N CH₂CH₃ SCHF₂ 6-CF₃ CH H SCHF₂ 6-OCF₃ N CH₂CH₃ SCHF₂ 6-OCF₃ CH HOCF₃ 6-CF₃ N CH₂CH₃ OCF₃ 6-CF₃ CH H OCF₃ 6-OCF₃ N CH₂CH₃ OCF₃ 6-OCF₃ CHH SCF₃ 6-CF₃ N CH₂CH₃ SCF₃ 6-CF₃ CH H SCF₃ 6-OCF₃ N CH₂CH₃ SCF₃ 6-OCF₃CH H Cl 6-CF₃ N CH₂CH₃ Cl 6-CF₃ CH H Cl 6-OCF₃ N CH₂CH₃ Cl 6-OCF₃ CH CH₃CF₃ 6-CF₃ N CH₃ CF₃ 6-CF₃ CH CH₃ CF₃ 6-OCF₃ N CH₃ CF₃ 6-OCF₃ CH CH₃OCHF₂ 6-CF₃ N CH₃ OCHF₂ 6-CF₃ CH CH₃ OCHF₂ 6-OCF₃ N CH₃ OCHF₂ 6-OCF₃ CHCH₃ SCHF₂ 6-CF₃ N CH₃ SCHF₂ 6-CF₃ CH CH₃ SCHF₂ 6-OCF₃ N CH₃ SCHF₂ 6-OCF₃CH CH₃ OCF₃ 6-CF₃ N CH₃ OCF₃ 6-CF₃ CH CH₃ OCF₃ 6-OCF₃ N CH₃ OCF₃ 6-OCF₃CH CH₃ SCF₃ 6-CF₃ N CH₃ SCF₃ 6-CF₃ CH CH₃ SCF₃ 6-OCF₃ N CH₃ SCF₃ 6-OCF₃CH CH₃ Cl 6-CF₃ N CH₃ Cl 6-CF₃ CH CH₃ Cl 6-OCF₃ N CH₃ Cl 6-OCF₃ CH OCH₃CF₃ 6-CF₃ N OCH₃ CF₃ 6-CF₃ CH OCH₃ CF₃ 6-OCF₃ N OCH₃ CF₃ 6-OCF₃ CH OCH₃OCHF₂ 6-CF₃ N OCH₃ OCHF₂ 6-CF₃ CH OCH₃ OCHF₂ 6-OCF₃ N OCH₃ OCHF₂ 6-OCF₃CH OCH₃ SCHF₂ 6-CF₃ N OCH₃ SCHF₂ 6-CF₃ CH OCH₃ SCHF₂ 6-OCF₃ N OCH₃ SCHF₂6-OCF₃ CH OCH₃ OCF₃ 6-CF₃ N OCH₃ OCF₃ 6-CF₃ CH OCH₃ OCF₃ 6-OCF₃ N OCH₃OCF₃ 6-OCF₃ CH OCH₃ SCF₃ 6-CF₃ N OCH₃ SCF₃ 6-CF₃ CH OCH₃ SCF₃ 6-OCF₃ NOCH₃ SCF₃ 6-OCF₃ CH OCH₃ Cl 6-CF₃ N OCH₃ Cl 6-CF₃ CH OCH₃ Cl 6-OCF₃ NOCH₃ Cl 6-OCF₃ wherein Z is N and X and Y are CH CH H CF₃ 6-CF₃ N CH₂CH₃CF₃ 6-CF₃ CH H CF₃ 6-OCF₃ N CH₂CH₃ CF₃ 6-OCF₃ CH H OCHF₂ 6-CF₃ N CH₂CH₃OCHF₂ 6-CF₃ CH H OCHF₂ 6-OCF₃ N CH₂CH₃ OCHF₂ 6-OCF₃ CH H SCHF₂ 6-CF₃ NCH₂CH₃ SCHF₂ 6-CF₃ CH H SCHF₂ 6-OCF₃ N CH₂CH₃ SCHF₂ 6-OCF₃ CH H OCF₃6-CF₃ N CH₂CH₃ OCF₃ 6-CF₃ CH H OCF₃ 6-OCF₃ N CH₂CH₃ OCF₃ 6-OCF₃ CH HSCF₃ 6-CF₃ N CH₂CH₃ SCF₃ 6-CF₃ CH H SCF₃ 6-OCF₃ N CH₂CH₃ SCF₃ 6-OCF₃ CHH Cl 6-CF₃ N CH₂CH₃ Cl 6-CF₃ CH H Cl 6-OCF₃ N CH₂CH₃ Cl 6-OCF₃ CH CH₃CF₃ 6-CF₃ N CH₃ CF₃ 6-CF₃ CH CH₃ CF₃ 6-OCF₃ N CH₃ CF₃ 6-OCF₃ CH CH₃OCHF₂ 6-CF₃ N CH₃ OCHF₂ 6-CF₃ CH CH₃ OCHF₂ 6-OCF₃ N CH₃ OCHF₂ 6-OCF₃ CHCH₃ SCHF₂ 6-CF₃ N CH₃ SCHF₂ 6-CF₃ CH CH₃ SCHF₂ 6-OCF₃ N CH₃ SCHF₂ 6-OCF₃CH CH₃ OCF₃ 6-CF₃ N CH₃ OCF₃ 6-CF₃ CH CH₃ OCF₃ 6-OCF₃ N CH₃ OCF₃ 6-OCF₃CH CH₃ SCF₃ 6-CF₃ N CH₃ SCF₃ 6-CF₃ CH CH₃ SCF₃ 6-OCF₃ N CH₃ SCF₃ 6-OCF₃CH CH₃ Cl 6-CF₃ N CH₃ Cl 6-CF₃ CH CH₃ Cl 6-OCF₃ N CH₃ Cl 6-OCF₃ CH OCH₃CF₃ 6-CF₃ N OCH₃ CF₃ 6-CF₃ CH OCH₃ CF₃ 6-OCF₃ N OCH₃ CF₃ 6-OCF₃ CH OCH₃OCHF₂ 6-CF₃ N OCH₃ OCHF₂ 6-CF₃ CH OCH₃ OCHF₂ 6-OCF₃ N OCH₃ OCHF₂ 6-OCF₃CH OCH₃ SCHF₂ 6-CF₃ N OCH₃ SCHF₂ 6-CF₃ CH OCH₃ SCHF₂ 6-OCF₃ N OCH₃ SCHF₂6-OCF₃ CH OCH₃ OCF₃ 6-CF₃ N OCH₃ OCF₃ 6-CF₃ CH OCH₃ OCF₃ 6-OCF₃ N OCH₃OCF₃ 6-OCF₃ CH OCH₃ SCF₃ 6-CF₃ N OCH₃ SCF₃ 6-CF₃ CH OCH₃ SCF₃ 6-OCF₃ NOCH₃ SCF₃ 6-OCF₃ CH OCH₃ Cl 6-CF₃ N OCH₃ Cl 6-CF₃ CH OCH₃ Cl 6-OCF₃ NOCH₃ Cl 6-OCF₃

TABLE 3

W R¹ R³ R⁴ W R¹ R³ R⁴ wherein X is N and Y and Z are CH CH H CH₃ 2-CF₃ NCH₂CH₃ CF₃ 2-CF₃ CH H CF₃ 2-OCF₃ N CH₂CH₃ CF₃ 2-OCF₃ CH H OCHF₂ 2-CF₃ NCH₂CH₃ OCHF₂ 2-CF₃ CH H OCHF₂ 2-OCF₃ N CH₂CH₃ OCHF₂ 2-OCF₃ CH H SCHF₂2-CF₃ N CH₂CH₃ SCHF₂ 2-CF₃ CH H SCHF₂ 2-OCF₃ N CH₂CH₃ SCF₂ 2-OCF₃ CH HOCF₃ 2-CF₃ N CH₂CH₃ OCF₃ 2-CF₃ CH H OCF₃ 2-OCF₃ N CH₂CH₃ OCF₃ 2-OCF₃ CHH SCF₃ 2-CF₃ N CH₂CH₃ SCF₃ 2-CF₃ CH H SCF₃ 2-OCF₃ N CH₂CH₃ SCF₃ 2-OCF₃CH H Cl 2-CF₃ N CH₂CH₃ Cl 2-CF₃ CH H Cl 2-OCF₃ N CH₂CH₃ Cl 2-OCF₃ CH CH₃CF₃ 2-CF₃ N CH₃ CF₃ 2-CF₃ CH CH₃ CF₃ 2-OCF₃ N CH₃ CF₃ 2-OCF₃ CH CH₃OCHF₂ 2-CF₃ N CH₃ OCHF₂ 2-CF₃ CH CH₃ OCHF₂ 2-OCF₃ N CH₃ OCHF₂ 2-OCF₃ CHCH₃ SCHF₂ 2-CF₃ N CH₃ SCHF₂ 2-CF₃ CH CH₃ SCHF₂ 2-OCF₃ N CH₃ SCHF₂ 2-OCF₃CH CH₃ OCF₃ 2-CF₃ N CH₃ OCF₃ 2-CF₃ CH CH₃ OCF₃ 2-OCF₃ N CH₃ OCF₃ 2-OCF₃CH CH₃ SCF₃ 2-CF₃ N CH₃ SCF₃ 2-CF₃ CH CH₃ SCF₃ 2-OCF₃ N CH₃ SCF₃ 2-OCF₃CH CH₃ Cl 2-CF₃ N CH₃ Cl 2-CF₃ CH CH₃ Cl 2-OCF₃ N CH₃ Cl 2-OCF₃ CH OCH₃CF₃ 2-CF₃ N OCH₃ CF₃ 2-CF₃ CH OCH₃ CF₃ 2-OCF₃ N OCH₃ OF₃ 2-OCF₃ CH OCH₃OCHF₂ 2-CF₃ N OCH₃ OCHF₂ 2-CF₃ CH OCH₃ OCHF₂ 2-OCF₃ N OCH₃ OCHF₂ 2-OCF₃CH OCH₃ SCHF₂ 2-CF₃ N OCH₃ SCHF₂ 2-CF₃ CH OCH₃ SCHF₂ 2-OCF₃ N OCH₃ SCHF₂2-OCF₃ CH OCH₃ OCF₃ 2-CF₃ N OCH₃ OCF₃ 2-CF₃ CH OCH₃ OCF₃ 2-OCF₃ N OCH₃OCF₃ 2-OCF₃ CH OCH₃ SCF₃ 2-CF₃ N OCH₃ SCF₃ 2-CF₃ CH OCH₃ SCF₃ 2-OCF₃ NOCH₃ SCF₃ 2-OCF₃ CH OCH₃ Cl 2-CF₃ N OCH₃ Cl 2-CF₃ CH OCH₃ Cl 2-OCF₃ NOCH₃ Cl 2-OCF₃ wherein Z is N and X and Y are CH CH H CF₃ 2-CF₃ N CH₂CH₃CF₃ 2-CF₃ CH H CF₃ 2-OCF₃ N CH₂CH₃ CF₃ 2-OCF₃ CH H OCHF₂ 2-CF₃ N CH₂CH₃OCHF₂ 2-CF₃ CH H OCHF₂ 2-OCF₃ N CH₂CH₃ OCHF₂ 2-OCF₃ CH H SCHF₂ 2-CF₃ NCH₂CH₃ SCHF₂ 2-CF₃ CH H SCHF₂ 2-OCF₃ N CH₂CH₃ SCHF₂ 2-OCF₃ CH H OCF₃2-CF₃ N CH₂CH₃ OCF₃ 2-CF₃ CH H OCF₃ 2-OCF₃ N CH₂CH₃ OCF₃ 2-OCF₃ CH HSCF₃ 2-CF₃ N CH₂CH₃ SCF₃ 2-CF₃ CH H SCF₃ 2-9CF₃ N CH₂CH₃ SCF₃ 2-OCF₃ CHH Cl 2-CF₃ N CH₂CH₃ Cl 2-CF₃ CH H Cl 2-OCF₃ N CH₂CH₃ Cl 2-OCF₃ CH CH₃CF₃ 2-CF₃ N CH₃ CF₃ 2-CF₃ CH CH₃ CF₃ 2-OCF₃ N CH₃ CF₃ 2-OCF₃ CH CH₃OCHF₂ 2-CF₃ N CH₃ OCHF₂ 2-CF₃ CH CH₃ OCHF₂ 2-OCF₃ N CH₃ OCHF₂ 2-OCF₃ CHCH₃ SCHF₂ 2-CF₃ N CH₃ SCHF₂ 2-CF₃ CH CH₃ SCHF₂ 2-OCF₃ N CH₃ SCHF₂ 2-OCF₃CH CH₃ OCF₃ 2-CF₃ N CH₃ OCF₃ 2-CF₃ CH CH₃ OCF₃ 2-OCF₃ N CH₃ OCF₃ 2-OCF₃CH CH₃ SCF₃ 2-CF₃ N CH₃ SCF₃ 2-CF₃ CH CH₃ SCF₃ 2-OCF₃ N CH₃ SCF₃ 2-OCF₃CH CH₃ Cl 2-CF₃ N CH₃ Cl 2-CF₃ CH CH₃ Cl 2-OCF₃ N CH₃ Cl 2-OCF₃ CH OCH₃CF₃ 2-CF₃ N OCH₃ CF₃ 2-CF₃ CH OCH₃ CF₃ 2-OCF₃ N OCH₃ CF₃ 2-OCF₃ CH OCH₃OCHF₂ 2-CF₃ N OCH₃ OCHF₂ 2-CF₃ CH OCH₃ OCHF₂ 2-OCF₃ N OCH₃ OCHF₂ 2-OCF₃CH OCH₃ SCHF₂ 2-CF₃ N OCH₃ SCHF₂ 2-CF₃ CH OCH₃ SCHF₂ 2-OCF₃ N OCH₃ SCHF₂2-OCF₃ CH OCH₃ OCF₃ 2-CF₃ N OCH₃ OCF₃ 2-CF₃ CH OCH₃ OCF₃ 2-OCF₃ N OCH₃OCF₃ 2-OCF₃ CH OCH₃ SCF₃ 2-CF₃ N OCH₃ SCF₃ 2-CF₃ CH OCH₃ SCF₃ 2-OCF₃ NOCH₃ SCF₃ 2-OCF₃ CH OCH₃ Cl 2-CF₃ N OCH₃ Cl 2-CF₃ CH OCH₃ Cl 2-OCF₃ NOCH₃ Cl 2-OCF₃

TABLE 4

W R¹ R³ W R¹ R³ wherein X is N and Y and Z are CH CH H CF₃ N CH₂CH₃ CF₃CH H OCHF₂ N CH₂CH₃ OCHF₂ CH H SCHF₂ N CH₂CH₃ SCHF₂ CH H OCF₃ N CH₂CH₃OCF₃ CH H SCF₃ N CH₂CH₃ SCF₃ CH H Cl N CH₂CH₃ Cl CH CH₃ CF₃ N CH₃ CF₃ CHCH₃ OCHF₂ N CH₃ OCHF₂ CH CH₃ SCHF₂ N CH₃ SCHF₂ CH CH₃ OCF₃ N CH₃ OCF₃ CHCH₃ SCF₃ N CH₃ SCF₃ CH CH₃ Cl N CH₃ Cl CH OCH₃ CF₃ N OCH₃ CF₃ CH OCH₃OCHF₂ N OCH₃ OCHF₂ CH OCH₃ SCHF₂ N OCH₃ SCHF₂ CH OCH₃ OCF₃ N OCH₃ OCF₃CH OCH₃ SCF₃ N OCH₃ SCF₃ CH OCH₃ Cl N OCH₃ Cl wherein Z is N and X and Yare CH CH H CF₃ N CH₂CH₃ CF₃ CH H OCHF₂ N CH₂CH₃ OCHF₂ CH H SCHF₂ NCH₂CH₃ SCHF₂ CH H OCF₃ N CH₂CH₃ OCF₃ CH H SCF₃ N CH₂CH₃ SCF₃ CH H Cl NCH₂CH₃ Cl CH CH₃ CF₃ N CH₃ CF₃ CH CH₃ OCHF₂ N CH₃ OCHF₂ CH CH₃ SCHF₂ NCH₃ SCHF₂ CH CH₃ OCF₃ N CH₃ OCF₃ CH CH₃ SCF₃ N CH₃ SCF₃ CH CH₃ Cl N CH₃Cl CH OCH₃ CF₃ N OCH₃ CF₃ CH OCH₃ OCHF₂ N OCH₃ OCHF₂ CH OCH₃ SCHF₂ NOCH₃ SCHF₂ CH OCH₃ OCF₃ N OCH₃ OCF₃ CH OCH₃ SCF₃ N OCH₃ SCF₃ CH OCH₃ ClN OCH₃ Cl

TABLE 5

W R¹ R³ R⁷ R⁸ wherein X is N and Y and Z are CH CH H CF₃ CF₃ CH₃ CH HCF₃ CF₃ CH₂CF₃ CH H OCHF₂ CF₃ CH₃ CH H OCHF₂ CF₃ CH₂CF₃ CH H SCHF₂ CF₃CH₃ CH H SCHF₂ CF₃ CH₂CF₃ CH CH₃ CF₃ CF₃ CH₃ CH CH₃ CF₃ CF₃ CH₂CF₃ CHCH₃ OCHF₂ CF₃ CH₃ CH CH₃ OCHF₂ CF₃ CH₂CF₃ CH CH₃ SCHF₂ CF₃ CH₃ CH CH₃SCHF₂ CF₃ CH₂CF₃ CH OCH₃ CF₃ CF₃ CH₃ CH OCH₃ CF₃ CF₃ CH₂CF₃ CH OCH₃OCHF₂ CF₃ CH₃ CH OCH₃ OCHF₂ CF₃ CH₂CF₃ CH OCH₃ SCHF₂ CF₃ CH₃ CH OCH₃SCHF₂ CF₃ CH₂CF₃ N CH₂CH₃ CF₃ CF₃ CH₃ N CH₂CH₃ CF₃ CF₃ CH₂CF₃ N CH₂CH₃OCHF₂ CF₃ CH₃ N CH₂CH₃ OCHF₂ CF₃ CH₂CF₃ N CH₂CH₃ SCHF₂ CF₃ CH₃ N CH₂CH₃SCHF₂ CF₃ CH₂CF₃ N CH₃ CF₃ CF₃ CH₃ N CH₃ CF₃ CF₃ CH₂CF₃ N CH₃ OCHF₂ CF₃CH₃ N CH₃ OCHF₂ CF₃ CH₂CF₃ N CH₃ SCHF₂ CF₃ CH₃ N CH₃ SCHF₂ CF₃ CH₂CF₃ NOCH₃ CF₃ CF₃ CH₃ N OCH₃ CF₃ CF₃ CH₂CF₃ N OCH₃ OCHF₂ CF₃ CH₃ N OCH₃ OCHF₂CF₃ CH₂CF₃ N OCH₃ SCHF₂ CF₃ CH₃ N OCH₃ SCHF₂ CF₃ CH₂CF₃ CH H CF₃ OCHF₂CH₃ CH H CF₃ OCHF₂ CH₂CF₃ CH H OCHF₂ OCHF₂ CH₃ CH H OCHF₂ OCHF₂ CH₂CF₃CH H SCHF₂ OCHF₂ CH₃ CH H SCHF₂ OCHF₂ CH₂CF₃ CH CH₃ CF₃ OCHF₂ CH₃ CH CH₃CF₃ OCHF₂ CH₂CF₃ CH CH₃ OCHF₂ OCHF₂ CH₃ CH CH₃ OCHF₂ OCHF₂ CH₂CF₃ CH CH₃SCHF₂ OCHF₂ CH₃ CH CH₃ SCHF₂ OCHF₂ CH₂CF₃ CH OCH₃ CF₃ OCHF₂ CH₃ CH OCH₃CF₃ OCHF₂ CH₂CF₃ CH OCH₃ OCHF₂ OCHF₂ CH₃ CH OCH₃ OCHF₂ OCHF₂ CH₂CF₃ CHOCH₃ SCHF₂ OCHF₂ CH₃ CH OCH₃ SCHF₂ OCF₂ CH₂CF₃ N CH₂CH₃ CF₃ OCHF₂ CH₃ NCH₂CH₃ CF₃ OCHF₂ CH₂CF₃ N CH₂CH₃ OCHF₂ OCHF₂ CH₃ N CH₂CH₃ OCHF₂ OCHF₂CH₂CF₃ N CH₂CH₃ SCHF₂ OCHF₂ CH₃ N CH₂CH₃ SCHF₂ OCHF₂ CH₂CF₃ N CH₃ CF₃OCHF₂ CH₃ N CH₃ CF₃ OCHF₂ CH₂CF₃ N CH₃ OCHF₂ OCHF₂ CH₃ N CH₃ OCHF₂ OCHF₂CH₂CF₃ N CH₃ SCHF₂ OCHF₂ CH₃ N CH₃ SCHF₂ OCHF₂ CH₂CF₃ N OCH₃ CF₃ OCHF₂CH₃ N OCH₃ CF₃ OCHF₂ CH₂CF₃ N OCH₃ OCHF₂ OCHF₂ CH₃ N OCH₃ OCHF₂ OCHF₂CH₂CF₃ N OCH₃ SCHF₂ OCHF₂ CH₃ N OCH₃ SCHF₂ OCHF₂ CH₂CF₃ CH H CF₃ SCHF₂CH₃ CH H CF₃ SCHF₂ CH₂CF₃ CH H OCHF₂ SCHF₂ CH₃ CH H OCHF₂ SCHF₂ CH₂CF₃CH H SCHF₂ SCHF₂ CH₃ CH H SCHF₂ SCHF₂ CH₂CF₃ CH CH₃ CF₃ SCHF₂ CH₃ CH CH₃CF₃ SCHF₂ CH₂CF₃ CH CH₃ OCHF₂ SCHF₂ CH₃ CH CH₃ OCHF₂ SCHF₂ CH₂CF₃ CH CH₃SCHF₂ SCHF₂ CH₃ CH CH₃ SCHF₂ SCHF₂ CH₂CF₃ CH OCH₃ CF₃ SCHF₂ CH₃ CH OCH₃CF₃ SCHF₂ CH₂CF₃ CH OCH₃ OCHF₂ SCHF₂ CH₃ CH OCH₃ OCHF₂ SCHF₂ CH₂CF₃ CHOCH₃ SCHF₂ SCHF₂ CH₃ CH OCH₃ SCHF₂ SCHF₂ CH₂CF₃ N CH₂CH₃ CF₃ SCHF₂ CH₃ NCH₂CH₃ CF₃ SCHF₂ CH₂CF₃ N CH₂CH₃ OCHF₂ SCHF₂ CH₃ N CH₂CH₃ OCHF₂ SCHF₂CH₂CF₃ N CH₂CH₃ SCHF₂ SCHF₂ CH₃ N CH₂CH₃ SCHF₂ SCHF₂ CH₂CF₃ N CH₃ CF₃SCHF₂ CH₃ N CH₃ CF₃ SCHF₂ CH₂CF₃ N CH₃ OCHF₂ SCHF₂ CH₃ N CH₃ OCHF₂ SCHF₂CH₂CF₃ N CH₃ SCHF₂ SCHF₂ CH₃ N CH₃ SCHF₂ SCHF₂ CH₂CF₃ N OCH₃ CF₃ SCHF₂CH₃ N OCH₃ CF₃ SCHF₂ CH₂CF₃ N OCH₃ OCHF₂ SCHF₂ CH₃ N OCH₃ OCHF₂ SCHF₂CH₂CF₃ N OCH₃ SCHF₂ SCHF₂ CH₃ N OCH₃ SCHF₂ SCHF₂ CH₂CF₃ wherein Z is Nand X and Y are CH CH H CF₃ CF₃ CH₃ CH H CF₃ CF₃ CH₂CF₃ CH H OCHF₂ CF₃CH₃ CH H OCHF₂ CF₃ CH₂CF₃ CH H SCHF₂ CF₃ CH₃ CH H SCHF₂ CF₃ CH₂CF₃ CHCH₃ CF₃ CF₃ CH₃ CH CH₃ CF₃ CF₃ CH₂CF₃ CH CH₃ OCHF₂ CF₃ CH₃ CH CH₃ OCHF₂CF₃ CH₂CF₃ CH CH₃ SCHF₂ CF₃ CH₃ CH CH₃ SCHF₂ CF₃ CH₂CF₃ CH OCH₃ CF₃ CF₃CH₃ CH OCH₃ CF₃ CF₃ CH₂CF₃ CH OCl13 OCHF₂ CF₃ CH₃ CH OCH₃ OCHF₂ CF₃CH₂CF₃ CH OCH₃ SCHF₂ CF₃ CH₃ CH OCH₃ SCHF₂ CF₃ CH₂CF₃ N CH₂CH₃ CF₃ CF₃CH₃ N CH₂CH₃ CF₃ CF₃ CH₂CF₃ N CH₂CH₃ OCHF₂ CF₃ CH₃ N CH₂CH₃ OCHF₂ CF₃CH₂CF₃ N CH₂CH₃ SCHF₂ CF₃ CH₃ N CH₂CH₃ SCHF₂ CF₃ CH₂CF₃ N CH₃ CF₃ CF₃CH₃ N CH₃ CF₃ CF₃ CH₂CF₃ N CH₃ OCHF₂ CF₃ CH₃ N CH₃ OCHF₂ CF₃ CH₂CF₃ NCH₃ SCHF₂ CF₃ CH₃ N CH₃ SCHF₂ CF₃ CH₂CF₃ N OCH₃ CF₃ CF₃ CH₃ N OCH₃ CF₃CF₃ CH₂CF₃ N OCH₃ OCHF₂ CF₃ CH₃ N OCH₃ OCHF₂ CF₃ CH₂CF₃ N OCH₃ SCHF₂ CF₃CH₃ N OCH₃ SCHF₂ CF₃ CH₂CF₃ CH H CF₃ OCHF₂ CH₃ CH H CF₃ OCHF₂ CH₂CF₃ CHH OCHF₂ OCHF₂ CH₃ CH H OCHF₂ OCHF₂ CH₂CF₃ CH H SCHF₂ OCHF₂ CH₃ CH HSCHF₂ OCHF₂ CH₂CF₃ CH CH₃ CF₃ OCHF₂ CH₃ CH CH₃ CF₃ OCHF₂ CH₂CF₃ CH CH₃OCHF₂ OCHF₂ CH₃ CH CH₃ OCHF₂ OCHF₂ CH₂CF₃ CH CH₃ SCHF₂ OCHF₂ CH₃ CH CH₃SCHF₂ OCHF₂ CH₂CF₃ CH OCH₃ CF₃ OCHF₂ CH₃ CH OCH₃ CF₃ OCHF₂ CH₂CF₃ CHOCH₃ OCHF₂ OCHF₂ CH₃ CH OCH₃ OCHF₂ OCHF₂ CH₂CF₃ CH OCH₃ SCHF₂ OCHF₂ CH₃CH OCH₃ SCHF₂ OCHF₂ CH₂CF₃ N CH₂CH₃ CF₃ OCHF₂ CH₃ N CH₂CH₃ CF₃ OCHF₂CH₂CF₃ N CH₂CH₃ OCHF₂ OCHF₂ CH₃ N CH₂CH₃ OCHF₂ OCHF₂ CH₂CF₃ N CH₂CH₃SCHF₂ OCHF₂ CH₃ N CH₂CH₃ SCHF₂ OCHF₂ CH₂CF₃ N CH₃ CF₃ OCHF₂ CH₃ N CH₃CF₃ OCHF₂ CH₂CF₃ N CH₃ OCHF₂ OCHF₂ CH₃ N CH₃ OCHF₂ OCHF₂ CH₂CF₃ N CH₃SCHF₂ OCHF₂ CH₃ N CH₃ SCHF₂ OCHF₂ CH₂CF₃ N OCH₃ CF₃ OCHF₂ CH₃ N OCH₃ CF₃OCHF₂ CH₂CF₃ N OCH₃ OCHF₂ OCHF₂ CH₃ N OCH₃ OCHF₂ OCHF₂ CH₂CF₃ N OCH₃SCHF₂ OCHF₂ CH₃ N OCH₃ SCHF₂ OCHF₂ CH₂CF₃ CH H CF₃ SCHF₂ CH₃ CH H CF₃SCHF₂ CH₂CF₃ CH H OCHF₂ SCHF₂ CH₃ CH H OCHF₂ SCHF₂ CH₂CF₃ CH H SCHF₂SCHF₂ CH₃ CH H SCHF₂ SCHF₂ CH₂CF₃ CH CH₃ CF₃ SCHF₂ CH₃ CH CH₃ CF₃ SCHF₂CH₂CF₃ CH CH₃ OCHF₂ SCHF₂ CH₃ CH CH₃ OCHF₂ SCHF₂ CH₂CF₃ CH CH₃ SCHF₂SCHF₂ CH₃ CH CH₃ SCHF₂ SCHF₂ CH₂CF₃ CH OCH₃ CF₃ SCHF₂ CH₃ CH OCH₃ CF₃SCHF₂ CH₂CF₃ CH OCH₃ OCHF₂ SCHF₂ CH₃ CH OCH₃ OCHF₂ SCHF₂ CH₂CF₃ CH OCH₃SOHF₂ SCHF₂ CH₃ CH OCH₃ SCHF₂ SCHF₂ CH₂CF₃ N CH₂CH₃ CF₃ SCHF₂ CH₃ NCH₂CH₃ CF₃ SCHF₂ CH₂CF₃ N CH₂CH₃ OCHF₂ SCHF₂ CH₃ N CH₂CH₃ OCHF₂ SCHF₂CH₂CF₃ N CH₂CH₃ SCHF₂ SCHF₂ CH₃ N CH₂CH₃ SCHF₂ SCHF₂ CH₂CF₃ N CH₃ CF₃SCHF₂ CH₃ N CH₃ CF₃ SCHF₂ CH₂CF₃ N CH₃ OCHF₂ SCHF₂ CH₃ N CH₃ OCHF₂ SCHF₂CH₂CF₃ N CH₃ SCHF₂ SCHF₂ CH₃ N CH₃ SCHF₂ SCHF₂ CH₂CF₃ N OCH₃ CF₃ SCHF₂CH₃ N OCH₃ CF₃ SCHF₂ CH₂CF₃ N OCH₃ OCHF₂ SCHF₂ CH₃ N OCH₃ OCHF₂ SCHF₂CH₂CF₃ N OCH₃ SCHF₂ SCHF₂ CH₃ N OCH₃ SCHF₂ SCHF₂ CH₂CF₃

Formulation/Utility

Compounds of this invention will generally be used as a formulation orcomposition with an agriculturally suitable carrier comprising at leastone of a liquid diluent, a solid diluent or a surfactant. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature. Useful formulations include liquids such as solutions(including emulsifiable concentrates), suspensions, emulsions (includingmicroemulsions and/or suspoemulsions) and the like which optionally canbe thickened into gels. Useful formulations further include solids suchas dusts, powders, granules, pellets, tablets, films, and the like whichcan be water-dispersible (“wettable”) or water-soluble. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. Sprayableformulations can be extended in suitable media and used at spray volumesfrom about one to several hundred liters per hectare. High-strengthcompositions are primarily used as intermediates for furtherformulation.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand  5-90 0-92 1-15 Water-soluble Granules, Tablets and Powders.Suspensions, Emulsions,  5-50 20-95  0-15 Solutions (includingEmulsifiable Concentrates) Dusts  1-25 70-99  0-5  Granules and Pellets0.01-99     5-99.99 0-15 High Strength Compositions 90-99 0-10 0-2 

Typical solid diluents are described in Watkins, et al., Handbook ofInsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents are described in Marsden,Solvents Guide, 2nd Ed., Interscience, N.Y., 1950. McCutcheon 'sDetergents and Emulsifters Annual, Allured Publ. Corp., Ridgewood, N.J.,as well as Sisely and Wood, Encyclopedia of Surface Active Agents,Chemical Publ. Co., Inc., New York, 1962, list surfactants andrecommended uses. All formulations can contain minor amounts ofadditives to reduce foam, caking, corrosion, microbiological growth andthe like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols,polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acidesters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzenesulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates,naphthalene sulfonate formaldehyde condensates, polycarboxylates, andpolyoxyethylene/polyoxypropylene block copolymers. Solid diluentsinclude, for example, clays such as bentonite, montmorillonite,attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth,urea, calcium carbonate, sodium carbonate and bicarbonate, and sodiumsulfate. Liquid diluents include, for example, water,N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethyleneglycol, polypropylene glycol, paraffins, alkylbenzenes,alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn,peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters,ketones such as cyclohexanone, 2-heptanone, isophorone and2-hydroxy-2-methyl-2-pentanone, and alcohols such as methanol,cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. Dusts and powders can be prepared byblending and, usually, grinding as in a hammer mill or fluid-energymill. Suspensions are usually prepared by wet-milling; see, for example,U.S. Pat. No. 3,060,082. Granules and pellets can be prepared byspraying the active material upon preformed granular carriers or byagglomeration techniques. See Browning, “Agglomeration”, ChemicalEngineering, Dec. 2, 1967, pp 127-28, Perry 's Chemical Engineer'sHandbook, 2nd Ed., McGraw-Hill, N.Y., 1963, pages 8-57 and following,and WO 91/13526. Pellets can be prepared as described in U.S. Pat. No.2,172,712. Water-dispersible and water-soluble granules can be preparedas taught in U.S. Pat. No. 2,122,050, U.S. Pat. No. 3,920,222 and DE3,226,293. Tablets can be prepared as taught in U.S. Pat. No. 5,180,587,U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can beprepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see U.S. Pat.No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples10-21; U.S. Pat. No. 3,309,192, Col. 5, line 23 through Col. 7, line 62and Examples 8, 12, 15, 39, 21, 52, 53, 58, 132, 138-120, 162-162, 166,167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col.5, line 17 and Examples 1-2; Klingman, Weed Control as a Science, JohnWiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., WeedControl Handbook, 5th Ed., Blackwell Scientific Publications, Oxford,1989.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-D.

Example A High Strength Concentrate Compound 20 98.5% silica aerogel 0.5% synthetic amorphous fine silica  1.0%. Example B Wettable PowderCompound 49 65.0% dodecylphenol polyethylene glycol ether  2.0% sodiumligninsulfonate  2.0% sodium silicoaluminate  6.0% montmorillionite(calcined) 23.0%. Example C Granule Compound 12 10.0% attapulgitegranules (low volatile matter, 90.0%. 0.71/0.30 mm; U.S.S. No. 25-50sieves) Example D Extruded Pellet Compound 56 25.0% anhydrous sodiumsulfate 10.0% crude calcium ligninsulfonate  5.0% sodiumalkylnaphthalenesulfonate  1.0% calcium/magnesium bentonite 59.0%.

Test results indicate that the compounds of the present invention arehighly active preemergent and postemergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre- and/orpostemergence weed control in areas where complete control of allvegetation is desired such as around fuel storage tanks, industrialstorage areas, parking lots, drive-in theaters, air fields, river banks,irrigation and other waterways, around billboards and highway andrailroad structures. Some of the compounds are useful for the control ofselected grass and broadleaf weeds with tolerance to important agronomiccrops which include but are not limited to alfalfa, barley, cotton,wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats,peanuts, vegetables, tomato, potato, perennial plantation cropsincluding coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes,fruit trees, nut trees, banana, plantain, pineapple, hops, tea andforests such as eucalyptus and conifers (e.g., loblolly pine), and turfspecies (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescueand Bermuda grass). Those skilled in the art will appreciate that notall compounds are equally effective against all weeds. Alternatively,the subject compounds are useful to modify plant growth.

A herbicidally effective amount of the compounds of this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general, a herbicidally effective amount ofcompounds of this invention is 0.001 to 20 kg/ha with a preferred rangeof 0.002 to 1.0 kg/ha. One skilled in the art can easily determine theherbicidally effective amount necessary for the desired level of weedcontrol.

Compounds of this invention can be used alone or in combination withother commercial herbicides, insecticides or fungicides. Compounds ofthis invention can also be used in combination with commercial herbicidesafeners such as benoxacor, dichlormid and furilazole to increase safetyto certain crops. A mixture of one or more of the following herbicideswith a compound of this invention may be particularly useful for weedcontrol: acetochlor, acifluorfen and its sodium salt, aclonifen,acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole,ammonium sulfamate, anilofos, asulam, atrazine, azafenidin,azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate,bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and itssodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor,butralin, butroxydim (ICIA0500), butylate, caloxydim (BAS 620H),carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron,chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron,chlorpropham, chlorsulfuron, chlorthal-dimethyl, cinmethylin,cinosulfuron, clethodim, clomazone, clopyralid, clopyralid-olamine,cyanazine, cycloate, cyclosulfamuron, 2,2-D and its butotyl, butyl,isoctyl and isopropyl esters and its dimethylammonium, diolamine andtrolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,2-DB andits dimethylammonium, potassium and sodium salts, desmedipham,desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassiumand sodium salts, diclilobenil, dichlorprop, diclofop-methyl,2-[2,5-dihydro-2-methyl-2-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-methyl-3-pyridinecarboxylicacid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate,dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine,diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC.esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate,ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron,fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl,flazasulfuron, fluazifop-butyl, fluazifop-P-butyl, fluchloralin,flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron,fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodiumsalt, fluridone, flurochloridone, fluroxypyr, fluthiacet-methyl,fomesafen, fosamine-ammonium, glufosinate, glufosinate-ammonium,glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium,glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl,haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapyr,imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium,imazosulfuron, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon,isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleichydrazide, MCPA and its dimethylammonium, potassium and sodium salts,MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium,methabenzthiazuron, methylarsonic acid and its calcium, monoammonium,monosodium and disodium salts, methyl[[[1-[5-[2-chloro-2-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate(AKH-7088), methyl5-[[[[(2,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-1-(2-pyridinyl)-1H-pyrazole-2-carboxylate(NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin,metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam,neburon, nicosulfuron, norflurazon, oryzalin, oxadiazon, oxasulfuron,oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentoxazone(KPP-312), perfluidone, phenmedipham, picloram, picloram-potassium,pretilachlor, primisulfuron-methyl, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron,pyrazolynate, pyrazosulfuron-ethyl, pyridate, pyriminobac-methyl,pyrithiobac, pyrithiobac-sodium, quinclorac, quizalofop-ethyl,quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim,siduron, simazine, sulcotrione (ICIA005 1), sulfentrazone,sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil,terbuthylazine, terbutryn, thenylchior, thiafluamide (BAY 11390),thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate,triasulfuron, triaziflam, tribenuron-methyl, triclopyr,triclopyr-butotyl, triclopyr-triethylammnonium, tridiphane, trifluralin,triflusulfuron-methyl, and vernolate.

In certain instances, combinations with other herbicides having asimilar spectrum of control but a different mode of action will beparticularly advantageous for preventing the development of resistantweeds.

The following Tests demonstrate the control efficacy of the compounds ofthis invention against specific weeds. The weed control afforded by thecompounds is not limited, however, to these species. See Index TablesA-E for compound descriptions. The abbreviation “Ex.” stands for“Example” and is followed by a number indicating in which example thecompound is prepared.

INDEX TABLE A

Cmpd W R¹ R² X Y Z R³ mp (° C.)  1 (Ex. 1) CH H H N CH CH CF₃ 53-55  2CH H H CCl CH N Cl oil*  3 CH H H N CH CBr H 63-65  4 CH H H N CH N Cl83-86  5 CH H H CH CH N CF₃ 78-79  6 (Ex. 2) N H H N CH CH CF₃ 72-73  7N H H CCl CH N Cl 80-89  8 N H H N CCH₃ CH CF₃ 110-112  9 N H H N CH CBrH oil* 10 N H H N CH N Cl 83-86 11 N H CH₃ N CH CH CF₃ 93-95 12 (Ex. 3)N CH₃ H N CH CH CF₃ 113-115 13 N CH₃ H CH CH N CF₃ 63-66 14 N CH₃ H N CHCCl CF₃ 108-109 15 N CH₃ CH₃ N CH CH CF₃ 107-108 16 N CH₃ H N CH N CF₃114-115 17 N CH₃ H N CH CCN CF₃ 141-142 18 N CH₂CH₃ H N CH N CF₃ 97-98*See Index Table E for ¹H NMR data.

INDEX TABLE B

mp (° C.) Cmpd R¹ R³ R⁴ Q X Y Z or M + 1 19 CH₃ CF₃ OCF₃ O N CH CH 72-7320 CH₃ CF₃ OCF₃ O CH CH N oil* 21 CH₃ CF₃ CF₃ S N CH CH 101-102 22 CH₃CF₃ OCF₃ O N CH CCl 92-93 23 CH₃ CF₃ OCF₃ O N CH CCN 139-141 24 CH₃ CF₃OCF₃ O N CH N 95-97 25 CH₃ CF₃ SCF₃ O N CH CH 94-97 26 CH₃ CF₃ SCF₃ O CHCH N 73-77 27 CH₃ CF₃ SCF₃ O N CH CCl  98-101 28 CH₃ CF₃ Cl O N CH CH69-70 29 CH₃ C₂F₅ CF₃ O N CH CH 91-92 30 CH₃ CF₃ CF₃ O CH CCH₃ N 77-8131 CH₃ SO₂CH₂CH₃ CF₃ O N CH CH 117.5-119.5 32 CH₃ CF₃ CF₃ O CH CCH₂CH₃ N113-115 33 CH₃ CHF₂ CF₃ O N CH CH 67-72 34 CH₂CH₃ CF₃ CF₃ O CH CH N53-55 35 CH₂CH₃ CF₃ OCF₃ O CH CH N oil* 36 CH₂CH₃ CF₃ CF₃ O N CH CH108-109 37 CH₂CH₃ CF₃ OCF₃ O N CH CH 64-66 38 CH₃ CF₃ C(CH₃)₃ O N CH CH83-85 39 OCH₃ CF₃ CF₃ O N CH CH 109-111 40 OCH₃ CF₃ OCF₃ O N CH CH 94-9741 Br CF₃ CF₃ O N CH CH 139-142 42 CHF₂ CF₃ CF₃ O N CH CH 114-118 43CHBr₂ CF₃ CF₃ O N CH CH 106-108 44 CH₃ CF₃ CN O N CH CH m/z 346 45 CH₃CF₃ F O N CH CH m/z 339 46 CH₃ CF₃ I O N CH CH m/z 447 47 CH₃ H CF₃ O NCH Cl m/z 447 48 CH₃ H CN O N CH Cl m/z 404 *See Index Table E for ¹HNMR data.

INDEX TABLE C

Cmpd R¹ X Z mp (° C.) 49 CH₃ N CH 173-174 50 CH₃ CH N 145-146 51 CH₃ NCCl 178-179 52 CH₂CH₃ N CH 146-147 53 OCH₃ N CH 178-180 54 CH₂CH₃ N CCN103-108 55 CH₃ N N 150-151

INDEX TABLE D

Cmpd X Z mp (° C.) 56 N CH 170-172 57 N CCl 150-153 58 N N 149-150

INDEX TABLE E Cmpd No. ¹H NMR Data (CDCl₃ solution unless indicatedotherwise)^(a)  2 δ 7.06(d, 1H), 7.31(d, 1H), 7.35-7.60(m, 2H), 7.72(s,1H), 7.93(dd, 1H).  9 δ 6.85(d, 1H), 7.20-7.27(m, 1H), 7.50(s, 1H),7.58-7.65(m, 2H), 7.75(s, 1H), 8.18(s, 1H), 8.65(d, 1H). 20 δ 8.38(s,1H), 8.28(s, 1H), 7.89(s, 1H), 7.49(t, 1H), 7.25-7.10(m, 3H), 2.37(s,3H). 35 δ 8.41(s, 1H), 8.30(s, 1H), 7.90(s, 1H), 7.51(t, 1H), 7.23(d,1H), 7.18-7.10(m, 2H), 2.80(q, 2H), 1.37(t, 3H). ^(a1)H NMR data are inppm downfield from tetramethylsilane. Couplings are designated by(s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet,(dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broadsinglet.

BIOLOGICAL EXAMPLES OF THE INVENTION

Test A

Seeds of broadleaf signalgrass (Brachiaria decumbens), barley (Hordeumvulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galiumaparine), blackgrass (Alopecurus myosuroides), chickweed (Stellariamedia), cocklebur (Xanthium strumarium), corn (Zea mays), cotton(Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome(Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters(Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassicanapus), redroot pigweed (Amaranthus retroflexus), rice (Oryza sativa),sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Betavulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum),wild buckwheat (Polygonum convolvulus), wild oat (Avena fatua) andpurple nutsedge (Cyperus rotundus) tubers were planted and treatedpreemergence with test chemicals formulated in a non-phytotoxic solventmixture which included a surfactant. A sprayed paddy pot was treatedwith some designated compounds. This paddy contained rice,barnyardgrass, smallflowered flatsedge (Cyperus difformis) and ducksalad (Heteranthera limosa) as the target species and was sprayedalongside the other crop and weed species.

At the same time, these crop and weed species were also treated withpostemergence, applications of test chemicals formulated in the samemanner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) forpostemergence treatments. Treated plants and controls were maintained ina greenhouse for twelve to sixteen days, after which all species werecompared to controls and visually evaluated. Plant response ratings,summarized in Table A, arc basced on a scale of 0 to 10 where 0 is noeffect and 10 is complete control. A dash (-) response means no testresult.

TABLE A COMPOUND COMPOUND Rate 2000 g/ha 1 2 3 4 5 6 7 11 Rate 1000 g/ha13 14 19 49 POSTEMERGENCE POSTEMERGENCE B. signalgrass — — — — — — — —B. signalgrass 10 8 7 8 Barley 6 3 2 5 5 5 4 2 Barley — — — —Barnyardgrass 4 3 6 7 9 8 4 3 Barnyardgrass — — — — Bedstraw 9 9 10 10 99 9 3 Bedstraw 9 10 9 9 Blackgrass 8 4 3 5 8 9 3 3 Blackgrass 8 9 6 8Chickweed 7 6 6 9 9 9 6 5 Chickweed — — — — Cocklebur 7 6 4 7 8 8 8 6Cocklebur 9 10 8 9 Corn 3 2 2 3 3 3 2 3 Corn 6 4 7 8 Cotton 8 6 10 8 109 9 8 Cotton — — — — Crabgrass 8 4 8 9 9 9 6 8 Crabgrass 9 10 9 9 Downybrome 3 3 2 3 6 5 3 2 Downy brome — — — — Giant foxtail 4 3 4 9 9 9 4 6Giant foxtail 9 10 9 9 Lambsquarters 9 8 9 9 9 9 7 9 Lambsquarters — — —— Morningglory 9 4 9 7 9 9 9 8 Morningglory 10 10 8 9 Nutsedge 2 — 0 — 22 0 0 Nutsedge 2 3 0 3 Rape 8 7 9 10 10 10 9 9 Rape 10 10 9 10 Redrootpigweed — — — — — — — — Redroot pigweed 9 10 9 9 Rice 3 2 3 3 4 3 1 3Rice — — — — Sorghum 4 2 3 3 4 4 2 2 Sorghum — — — — Soybean 9 3 5 6 8 98 8 Soybean 10 10 8 10 Sugar beet 9 8 10 10 10 10 9 9 Sugar beet 9 10 99 Velvetleaf 7 7 7 7 9 9 7 1 Velvetleaf 9 9 7 9 Wheat 0 2 2 3 4 3 2 1Wheat 5 4 3 3 Wild buckwheat 7 8 5 9 8 9 10 6 Wild buckwheat — — — —Wild oat 4 3 4 4 5 5 4 3 Wild oat 7 9 8 8 COMPOUND COMPOUND Rate 2000g/ha 1 2 3 4 5 6 7 11 Rate 1000 g/ha 13 14 19 49 PREEMERGENCEPREEMERGENCE B. signalgrass — — — — — — — — B. signalgrass 10 10 10 10Barley 6 0 0 2 5 8 1 2 Barley — — — — Barnyardgrass 9 0 9 9 9 10 3 9Barnyardgrass — — — — Bedstraw 8 1 8 4 10 8 3 8 Bedstraw 10 10 9 10Blackgrass 10 0 8 10 9 10 4 10 Blackgrass 10 10 9 10 Chickweed 9 4 5 810 10 2 9 Chickweed — — — Cocklebur 0 0 0 0 3 2 0 0 Cocklebur 8 7 2 6Corn 2 0 0 1 2 3 0 1 Corn 5 4 7 7 Cotton 3 2 2 1 7 4 0 0 Cotton — — — —Crabgrass 10 1 9 10 10 10 9 10 Crabgrass 10 10 10 10 Downy brome 10 0 27 9 10 2 5 Downy brome — — — — Giant foxtail 10 2 9 10 10 10 9 10 Giantfoxtail 10 10 10 10 Lambsquarters 9 9 9 9 10 10 8 10 Lambsquarters — — —— Morningglory 3 1 2 4 8 10 3 3 Morningglory 10 10 10 10 Nutsedge — 0 00 0 — — — Nutsedge 0 1 0 1 Rape 8 2 2 4 9 10 6 7 Rape 10 10 10 10Redroot pigweed — — — — — — — — Redroot pigweed 10 10 10 10 Rice 2 0 0 02 1 0 0 Rice — — — — Sorghum 7 0 0 2 1 4 0 4 Sorghum — — — — Soybean 1 00 0 2 4 0 1 Soybean 6 5 3 7 Sugar beet 10 0 3 9 10 10 6 10 Sugar beet 1010 10 10 Velvetleaf 2 0 0 1 10 10 2 2 Velvetleaf 10 10 10 10 Wheat 9 0 02 7 9 0 1 Wheat 7 9 2 7 Wild buckwheat 5 1 1 6 9 10 2 8 Wild buckwheat —— — — Wild oat 10 3 7 9 9 10 5 10 Wild oat 10 10 10 10 COMPOUND Rate 400g/ha 1 2 3 4 5 6 7 8 10 11 POSTEMERGENCE B. signalgrass — — — — — — — —— — Barley 3 2 2 3 3 3 3 0 3 2 Barnyardgrass 2 2 2 2 7 3 2 0 0 2Bedstraw 9 7 8 7 7 8 9 1 7 2 Blackgrass 3 3 2 3 4 3 2 0 3 1 Chickweed 55 2 4 7 8 5 0 4 3 Cocklebur 6 5 4 6 7 5 5 0 5 4 Corn 2 1 2 2 2 2 0 0 1 2Cotton — 6 7 8 9 9 9 0 3 8 Crabgrass 5 3 4 7 7 9 3 0 2 6 Downybrome 1 31 2 3 3 2 0 2 0 Giant foxtail 2 3 2 3 6 6 2 0 1 3 Lambsquarters 8 8 6 99 9 7 0 3 9 Morningglory 8 4 8 7 8 9 7 1 2 7 Nutsedge 1 0 0 0 0 2 0 0 00 Rape 6 7 6 8 7 10 8 1 6 8 Redroot pigweed — — — — — — — — — — Rice 2 22 2 2 2 1 0 1 2 Sorghum 3 1 0 1 2 3 2 0 0 2 Soybean 6 3 3 5 7 9 4 2 2 6Sugar beet 9 8 9 9 9 9 8 1 7 9 Velvetleaf 2 6 5 1 8 8 2 0 2 1 Wheat 0 21 3 2 1 2 0 1 0 Wild buckwheat 7 7 2 9 4 8 7 1 0 3 Wild oat 3 2 1 2 3 42 0 2 2 COMPOUND Rate 400 g/ha 1 2 3 4 5 6 7 8 10 11 PREEMERGENCE B.signalgrass — — — — — — — — — — Barley 1 0 0 0 2 4 0 0 0 0 Barnyardgrass3 0 0 0 5 5 0 2 1 4 Bedstraw 3 0 0 — 6 8 0 0 0 0 Blackgrass 9 0 0 2 3 90 0 0 8 Chickweed 9 0 0 0 10 9 0 0 0 8 Cocklebur 0 0 0 0 1 0 0 0 0 0Corn 0 0 0 0 0 1 0 0 0 0 Cotton — 0 0 0 — 1 0 0 0 0 Crabgrass 9 0 3 6 910 3 2 8 9 Downy brome 6 0 0 0 4 6 0 0 0 1 Giant foxtail 10 1 4 6 7 10 40 3 9 Lambsquarters 9 3 0 0 9 10 2 0 0 9 Morningglory 2 0 0 0 8 6 0 0 02 Nutsedge 0 0 — — 0 — — — 0 0 Rape 2 0 0 0 8 9 0 0 0 3 Redroot pigweed— — — — — — — — — — Rice 0 0 0 0 0 0 0 2 0 0 Sorghum 2 0 0 0 0 2 0 0 0 2Soybean 0 0 0 0 1 2 0 0 0 0 Sugar beet 7 0 0 3 9 10 0 0 0 6 Velvetleaf 00 0 0 7 7 0 0 1 0 Wheat 2 0 0 0 2 3 0 0 0 0 Wild buckwheat 0 0 0 0 5 6 00 0 2 Wild oat 9 0 0 3 8 10 0 0 0 7 COMPOUND COMPOUND Rate 200 g/ha 1213 14 19 49 Rate 200 g/ha 12 13 14 19 49 POSTEMERGENCE PREEMERGENCE B.signalgrass — 4 3 4 5 B. signalgrass — 10 9 8 10 Barley 4 — — — — Barley5 — — — — Barnyardgrass 9 — — — — Barnyardgrass 10 — — — — Bedstraw 9 910 9 9 Bedstraw 7 8 10 10 9 Blackgrass 4 6 8 4 7 Blackgrass 10 10 10 910 Chickweed 8 — — — — Chickweed 9 — — — — Cocklebur 9 6 10 8 9Cocklebur 2 8 4 1 2 Corn 5 4 2 3 3 Corn 3 4 2 4 3 Cotton 10 — — — —Cotton 4 — — — — Crabgrass 9 8 10 8 9 Crabgrass 10 10 10 10 10 Downybrome 6 — — — — Downy brome 10 — — — — Giant foxtail 8 9 6 8 9 Giantfoxtail 10 10 10 10 10 Lambsquarters 9 — — — — Lambsquarters 10 — — — —Morningglory 9 8 10 8 9 Morningglory 8 6 10 9 5 Nutsedge 2 1 3 0 1Nutsedge 0 0 0 0 0 Rape 10 10 10 9 10 Rape 9 9 10 8 9 Redroot pigweed —9 10 9 9 Redroot pigweed — 10 10 10 10 Rice 3 — — — — Rice 2 — — — —Sorghum 4 — — — — Sorghum 7 — — — — Soybean 9 8 10 8 10 Soybean 0 2 4 14 Sugar beet 9 9 10 9 9 Sugar beet 10 10 10 10 10 Velvetleaf 9 9 9 7 9Velvetleaf 10 9 8 9 10 Wheat 3 3 3 1 2 Wheat 4 3 3 1 2 Wild buckwheat 8— — — — Wild buckwheat 4 — — — — Wild oat 7 3 5 4 4 Wild oat 10 10 9 810 COMPOUND COMPOUND COMPOUND Rate 100 g/ha 8 10 Rate 100 g/ha 8 10 Rate50 g/ha 9 12 POSTEMERGENCE PREEMERGENCE POSTEMERGENCE B. signalgrass — —B. signalgrass — — B. signalgrass — — Barley 0 2 Barley 0 0 Barley 0 3Barnyardgrass 0 0 Barnyardgrass 0 0 Barnyardgrass 0 5 Bedstraw 0 4Bedstraw 0 0 Bedstraw 3 9 Blackgrass 0 2 Blackgrass 0 0 Blackgrass 0 3Chickweed 0 2 Chickweed 0 0 Chickweed 3 7 Cocklebur 0 3 Cocklebur 0 0Cocklebur 2 7 Corn 0 0 Corn 0 0 Corn 1 3 Cotton 0 1 Cotton 0 0 Cotton 210 Crabgrass 0 1 Crabgrass 0 0 Crabgrass 0 8 Downy brome 0 1 Downy brome0 0 Downy brome 0 6 Giant foxtail 0 0 Giant foxtail 0 1 Giant foxtail 04 Lambsquarters 0 2 Lambsquarters 0 0 Lambsquarters 1 9 Morningglory 0 2Morningglory 0 0 Morningglory 2 8 Nutsedge 0 0 Nutsedge 0 0 Nutsedge 0 0Rape 0 5 Rape 0 0 Rape 3 10 Redroot pigweed — — Redroot pigweed — —Redroot pigweed — — Rice 0 0 Rice 0 0 Rice 0 2 Sorghum 0 0 Sorghum 0 0Sorghum 0 2 Soybean 0 1 Soybean 0 0 Soybean 1 8 Sugar beet 0 4 Sugarbeet 0 0 Sugar beet 2 9 Velvetleaf 0 1 Velvetleaf 0 0 Velvetleaf 0 8Wheat 0 0 Wheat 0 0 Wheat 0 2 Wild buckwheat 0 0 Wild buckwheat 0 0 Wildbuckwheat 1 8 Wild oat 0 1 Wild oat 0 0 Wild oat 0 3 COMPOUND Giantfoxtail 0 10 Rate 50 g/ha 9 12 Lambsquarters 0 9 PREEMERGENCEMorningglory 0 5 B. signalgrass — — Nutsedge 0 0 Barley 0 1 Rape 0 7Barnyardgrass 0 8 Redroot pigweed — — Bedstraw 0 5 Rice 0 1 Blackgrass 08 Sorghum 0 3 Chickweed 0 9 Soybean 0 0 Cocklebur 0 2 Sugar beet 0 9Corn 0 2 Velvetleaf 0 10 Cotton 0 1 Wheat 0 1 Crabgrass 0 10 Wildbuckwheat 0 3 Downy brome 0 7 Wild oat 0 9 COMPOUND COMPOUND Rate 1000g/ha 13 14 19 49 Rate 200 g/ha 13 14 19 49 SPRAYED PADDY SPRAYED PADDYBarnyardgrass 9 9 8 9 Barnyardgrass 8 6 7 9 Ducksalad 8 7 6 9 Ducksalad5 7 4 5 Rice 9 5 6 9 Rice 5 3 5 7 S. flatsedge 9 9 8 9 S. flatsedge 8 88 9

Test B

Seeds of broadleaf signalgrass (Brachiaria decitie,bens), bedstraw(Galium aparille), blackgrass (Alopecurus myosuroides), cocklebur(Xailhium strumarium), corn (Zea mays), crabgrass (Digitariasangitinalis), giant foxtail (Setaria faberii), morningglory (Ipornoeahederacea), rape (Brassica napus), redroot pigweed (Amaranthusretroflexus), soybean (Glycine max), sugar beet (Beta vtilgaris),velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild oat(Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were plantedand treated preemergence with test chemicals formulated in anon-phytotoxic solvent mixture which included a surfactant.

At the same time, these crop and weed species were also treated withpostemergence applications of test chemicals formulated in the samemanner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) forpostemergence treatments. Plant species in the flood test consisted ofrice (Oryza sativa), smallflower flatsedge (Cyperus difformis), ducksalad (Heteranthera limosa) and bamyardgrass (Echinochloa crus-galli)grown to the 2-leaf stage for testing. Treated plants and controls weremaintained in a greenhouse for twelve to sixteen days, after which allspecies were compared to controls and visually evaluated. Plant responseratings, summarized in Table B, are based on a scale of 0 to 10 where 0is no effect and 10 is complete control. A dash (-) response means notest result.

TABLE B COMPOUND COMPOUND Rate 1000 g/ha 5 26 Rate 1000 g/ha 5 26Postemergence Preemergence B. signalgrass 3 8 B. signalgrass 9 9Barnyardgrass 8 6 Blackgrass 9 10 Blackgrass 5 9 Cocklebur 2 8 Cocklebur8 10 Corn 3 3 Corn 3 6 Crabgrass 10 10 Crabgrass 10 8 Galium 10 7Ducksalad 7 6 Giant foxtail 10 10 Galium 10 10 Morningglory 10 10 Giantfoxtail 7 8 Nutsedge 10 0 Morningglory 9 9 Rape 10 10 Nutsedge 0 2Redroot pigweed 10 10 Rape 10 10 Soybean 1 8 Redroot pigweed 10 9Sugarbeets 10 10 Rice 5 5 Velvetleaf 9 10 S. Flatsedge 8 9 Wheat 4 2Soybean 6 9 Wild oats 10 9 Sugarbeets 10 10 Velvetleaf 8 10 Wheat 4 3Wild oats 5 7 COMPOUND Rate 500 g/ha 5 15 20 21 26 29 30 31Postemergence B. signalgrass 2 3 3 — 8 6 9 2 Barnyardgrass 6 0 6 0 6 7 64 Blackgrass 2 3 8 9 8 9 6 2 Cocklebur 6 6 9 9 9 9 8 9 Corn 2 2 6 2 4 33 2 Crabgrass 4 6 9 8 8 9 9 8 Ducksalad 6 2 5 2 4 8 4 1 Galium 10 5 9 910 9 10 7 Giant foxtail 3 3 9 7 8 9 9 6 Morningglory 9 8 10 8 9 10 8 9Nutsedge 0 0 1 0 2 — 0 2 Rape 10 8 9 9 10 9 10 8 Redroot pigweed 10 9 99 9 9 10 9 Rice 4 2 7 3 4 5 5 3 S. Flatsedge 7 4 9 8 9 9 9 9 Soybean 5 69 1 8 9 9 8 Sugarbeets 10 8 10 9 10 9 10 9 Velvetleaf 7 4 10 5 10 10 9 8Wheat 3 3 5 2 3 3 4 2 Wild oats 3 4 6 3 5 6 6 2 COMPOUND Rate 500 g/ha 515 20 21 26 29 30 31 Preemergence B. signalgrass 9 5 10 — 9 10 9 3Blackgrass 8 5 10 9 9 10 8 1 Cocklebur 0 0 9 1 8 9 7 3 Corn 0 0 3 1 2 31 0 Crabgrass 10 10 10 10 10 10 10 10 Galium 9 8 9 9 7 10 8 0 Giantfoxtai1 10 10 10 10 10 10 10 1 Morningglory 8 — 10 8 10 10 10 10Nutsedge 3 0 — 0 0 1 0 0 Rape 9 8 10 9 10 10 7 3 Redroot pigweed 10 9 1010 10 10 10 8 Soybean 0 0 7 0 6 3 4 1 Sugarbeets 10 8 10 10 10 10 10 10Velvetleaf 8 2 10 7 9 10 10 10 Wheat 2 0 8 1 2 9 3 1 Wild oats 8 7 10 99 10 9 1 COMPOUND Rate 5 12 13 14 15 16 17 19 20 21 22 23 24 25 26 27 2829 30 31 34 35 36 37 38 39 40 41 44 250 g/ha Post- emergence B. signal-2 — 4 3 3 8 3 3 2 — — 3 8 6 7 3 9 4 8 2 3 4 8 7 2 5 5 2 — grassBarnyard- 5 6 5 5 0 7 4 7 6 0 5 3 5 7 4 4 6 6 4 3 6 7 9 9 2 7 3 4 4grass Black- 2 9 8 6 2 9 7 4 6 6 8 4 8 8 6 7 8 5 3 1 4 4 8 7 2 6 7 2 —grass Cocklebur 6 9 9 9 6 10 9 8 9 9 9 8 8 9 9 8 9 9 8 — 8 9 9 9 2 8 108 — Corn 2 3 4 3 2 6 4 3 3 1 1 2 5 4 4 3 5 3 3 2 2 3 4 5 1 3 4 2 —Crabgrass 4 9 9 9 5 9 9 7 9 7 9 8 9 5 5 5 9 6 9 2 7 9 9 9 2 8 9 8 —Ducksalad 6 9 6 3 0 9 8 4 4 0 3 6 7 8 2 5 6 8 2 1 6 4 8 9 3 5 4 4 9Galium 7 9 9 9 4 — 10 9 9 8 9 9 9 9 7 9 10 9 10 7 9 — 9 9 — 10 — 10 —Giant 3 9 9 9 3 9 9 7 8 7 7 8 9 5 5 4 10 5 8 3 8 6 8 9 2 9 9 7 — foxtailMorning- 10 10 8 10 7 10 9 2 10 8 9 9 10 10 9 4 10 9 8 9 8 9 10 8 5 8 97 — glory Nutsedge 0 2 3 2 0 0 0 0 0 0 0 0 1 4 1 1 3 — 0 1 2 0 2 0 0 2 30 — Rape 8 10 9 10 8 9 10 7 10 9 10 8 10 10 10 10 10 9 10 8 9 9 9 9 3 1010 4 — Redroot 9 9 9 9 9 9 9 9 9 7 10 9 10 9 9 10 9 9 10 9 9 9 8 9 8 109 8 — pigweed Rice 3 6 5 6 0 8 3 7 6 2 3 2 6 5 3 3 5 4 5 2 2 3 7 7 1 6 44 4 S. 7 9 9 9 3 9 9 9 9 8 3 8 9 9 8 6 9 8 8 9 8 9 9 9 6 9 9 9 FlatsedgeSoybean 4 9 9 8 5 9 7 6 8 1 9 6 9 10 8 8 10 8 9 8 10 10 10 10 6 8 9 1 —Sugarbeets 9 9 9 9 8 9 10 9 10 9 9 9 10 10 10 10 10 9 10 9 9 9 9 8 7 1010 8 — Velvetleaf 7 9 9 9 3 9 8 7 9 5 9 6 9 9 9 8 9 9 8 6 9 9 9 9 3 8 82 — Wheat 2 2 4 3 2 3 1 2 2 1 3 2 2 4 2 2 3 3 3 2 1 1 4 4 1 3 4 2 — Wildoats 2 6 4 5 3 5 4 3 4 3 7 3 5 6 3 5 6 5 5 1 3 3 6 6 2 5 5 3 — COMPOUNDRate 250 g/ha 45 46 49 51 52 53 54 56 57 Postemergence B. signalgrass 48 5 — — — — 3 2 Barnyardgrass 6 5 6 0 6 1 3 7 4 Blackgrass 6 6 8 3 6 6 48 3 Cocklebur 6 9 10 6 7 6 8 7 8 Corn 4 4 4 3 6 1 4 7 2 Crabgrass — 1010 6 9 1 3 6 4 Ducksalad 5 2 8 0 4 0 2 9 6 Galium 7 9 9 9 9 7 8 9 9Giant foxtail 6 8 10 4 9 1 2 9 6 Morningglory 10 10 9 4 9 7 6 9 —Nutsedge 0 0 2 0 1 0 1 1 0 Rape 9 10 9 7 7 1 6 9 10 Redroot pigweed 9 109 9 9 8 9 10 9 Rice 3 5 6 0 5 0 2 8 4 S. Flatsedge 9 8 9 0 9 5 6 9 9Soybean — 7 9 5 8 2 7 6 4 Sugarbeets 9 10 9 8 9 7 9 9 9 Velvetleaf 8 8 93 6 5 7 9 7 Wheat 2 3 3 3 3 1 2 1 1 Wild oats 4 5 5 2 9 1 3 4 2 COMPOUNDRate 5 12 13 14 15 16 17 19 20 21 22 23 24 25 26 27 28 29 30 31 34 35 3637 38 39 40 41 45 250 g/ha Pre- emergence B. signal- 5 — 10 — 3 10 8 8 —— — 9 10 10 7 8 10 10 8 1 8 8 — — 2 9 9 8 9 grass Black- 1 10 10 9 1 1010 6 9 7 9 9 10 10 7 8 10 10 7 0 9 9 10 10 1 6 8 10 10 grass Cocklebur 09 8 6 0 7 4 3 7 0 2 8 10 8 3 3 2 5 — — 3 7 7 8 0 — 10 3 0 Corn 0 3 4 1 04 2 3 1 1 1 1 5 2 1 0 1 2 1 0 1 1 5 4 0 1 1 1 0 Crabgrass 8 10 10 10 210 10 10 10 10 10 10 10 10 9 9 10 10 10 9 9 10 10 10 4 10 10 10 10Galium 9 9 8 8 4 10 10 7 9 1 8 10 8 10 7 9 9 9 8 0 9 8 10 9 0 9 10 9 1Giant 9 10 10 10 7 10 10 10 10 10 10 10 10 10 9 9 10 10 10 9 10 10 10 104 10 10 10 9 foxtail Morning- 9 10 10 10 0 10 10 10 10 8 9 10 10 10 9 510 10 10 10 10 10 10 10 1 10 10 6 10 glory Nutsedge 0 1 0 0 0 — 0 0 0 00 1 0 4 0 — 5 1 — 0 1 1 1 — 0 — 1 — 0 Rape 8 10 10 10 5 10 10 9 10 8 1010 10 10 9 9 9 10 7 1 10 9 10 10 1 10 9 7 7 Redroot 10 10 10 10 5 10 109 10 10 10 10 10 10 10 10 10 10 10 6 10 10 10 10 8 10 10 10 10 pigweedSoybean 0 5 5 2 0 4 3 3 4 0 2 2 8 3 5 1 3 2 3 0 1 4 2 2 0 4 3 1 2Sugarbeets 9 10 10 10 7 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 1010 10 10 7 10 10 10 10 Velvetleaf 8 10 10 10 0 10 10 10 10 2 10 10 10 108 10 10 10 8 8 10 7 10 10 2 10 10 1 10 Wheat 0 3 4 5 0 4 2 2 4 0 6 3 6 11 3 1 3 2 0 2 3 4 5 0 2 4 4 0 Wild oats 6 10 10 10 2 10 8 8 9 7 10 8 1010 8 8 10 10 8 1 8 9 10 10 2 9 9 8 10 COMPOUND Rate 250 g/ha 46 49 51 5253 54 56 57 Preemergence B. signalgrass 9 10 3 — — — 9 8 Blackgrass 8 105 — 2 2 9 7 Cocklebur 2 8 2 7 0 2 3 0 Corn 1 5 0 5 0 0 4 0 Crabgrass 910 9 9 3 9 10 10 Galium 4 9 9 9 7 8 9 8 Giant foxtail 9 10 9 10 2 3 10 9Morningglory 9 10 10 8 6 7 10 10 Nutsedge 0 1 0 0 0 0 0 — Rape 7 10 8 91 2 10 10 Redroot pigweed 9 10 10 10 9 6 10 10 Soybean 1 5 1 2 0 1 1 1Sugarbeets 10 10 10 10 8 9 10 10 Velvetleaf 9 10 5 8 0 7 10 7 Wheat 4 43 3 0 1 4 1 Wild oats 9 10 3 9 2 4 10 9 COMPOUND Rate 5 12 13 14 15 1617 19 20 21 22 23 24 25 26 27 28 29 30 31 34 35 36 37 38 39 40 41 44 125g/ha Post- emergence B. signal- 1 — 3 3 3 6 2 2 2 — — 3 6 4 4 3 6 3 8 23 3 6 6 1 5 4 1 5 grass Barnyard- 3 5 4 4 0 6 3 5 5 0 4 2 4 6 4 3 5 4 43 5 4 8 8 1 6 3 3 3 grass Black- 1 7 6 5 2 8 5 4 5 — 7 3 3 7 3 7 6 3 3 13 4 7 6 1 5 6 1 5 grass Cocklebur 6 8 9 9 5 10 9 7 8 — 8 8 8 9 9 8 8 8 88 7 9 9 9 2 8 9 6 — Corn 2 2 2 2 2 4 4 1 3 — 1 1 5 4 3 3 3 3 3 2 2 3 4 51 2 3 1 4 Crabgrass 3 9 8 9 4 9 7 4 9 — 8 5 8 5 5 5 8 3 8 1 7 6 9 9 1 77 7 8 Ducksalad 4 9 — 3 0 8 8 2 3 0 2 4 6 7 2 4 4 7 0 0 3 3 5 9 2 4 3 38 Galium 7 9 9 9 4 10 10 8 9 — 9 — 9 9 7 — 10 9 10 4 9 — 9 9 7 10 — 8 9Giant 2 8 7 3 2 9 8 5 4 — 4 6 9 5 5 4 6 3 4 3 5 3 8 9 1 7 6 3 8 foxtailMorning- 7 10 8 10 6 9 9 2 9 — 9 7 9 10 6 4 10 6 8 9 8 9 9 8 2 8 9 3 9glory Nutsedge 0 1 1 1 0 0 0 0 0 — 0 0 0 3 0 0 1 0 0 0 1 0 2 0 0 1 0 0 0Rape 6 10 9 10 7 9 9 7 10 — 10 7 10 10 10 10 10 9 9 7 9 9 9 9 3 10 10 28 Redroot 8 9 9 9 9 9 9 9 9 — 9 9 10 9 9 10 9 9 8 9 9 9 8 8 5 10 9 8 9pigweed Rice 1 5 4 5 0 6 3 5 5 0 2 1 5 4 2 2 4 3 5 2 2 1 6 6 0 6 3 2 3S. 7 9 9 3 2 9 9 7 9 5 2 7 8 8 8 4 9 8 7 7 7 6 9 9 5 8 9 7 9 FlatsedgeSoybean 4 8 8 8 5 9 7 4 8 — 7 5 8 9 8 8 8 8 9 7 9 10 10 9 3 8 8 0 9Sugarbeets 9 9 9 9 8 9 9 9 10 — 9 9 10 9 10 9 10 9 10 8 9 9 9 8 4 10 9 810 Velvetleaf 7 9 9 9 3 9 8 3 9 — 9 6 9 9 9 8 9 8 8 6 9 9 9 8 2 8 8 0 9Wheat 2 2 3 2 1 2 1 2 2 — 1 1 1 3 2 2 3 3 2 2 1 1 3 4 1 2 3 1 4 Wildoats 2 3 4 4 3 4 2 2 3 — 7 3 4 5 3 5 5 4 3 1 2 3 6 5 1 5 4 2 4 COMPOUNDRate 125 g/ha 45 46 49 51 52 53 54 56 57 Postemergence B. signalgrass 48 4 — — — — 3 1 Barnyardgrass 3 4 5 0 5 0 2 7 4 Blackgrass 5 5 6 3 5 4 37 2 Cocklebur 4 9 10 5 5 6 8 6 7 Corn 4 3 3 2 5 0 3 5 2 Crabgrass 6 8 93 5 1 3 4 3 Ducksalad 5 2 8 0 3 0 2 9 5 Galium 7 9 9 8 8 8 8 9 9 Giantfoxtail 4 6 9 1 8 1 2 7 6 Morningglory 10 10 8 3 8 6 6 9 9 Nutsedge 0 02 0 0 0 0 0 0 Rape 8 8 9 7 7 0 5 9 8 Redroot pigweed 9 10 9 9 9 7 9 9 9Rice 3 4 5 0 4 0 0 8 4 S. Flatsedge 9 7 8 0 9 4 5 9 9 Soybean 9 7 8 4 60 4 6 2 Sugarbeets 9 10 9 8 9 7 9 9 9 Velvetleaf 7 8 9 3 6 2 6 8 7 Wheat2 3 2 2 3 1 1 1 1 Wild oats 3 4 5 2 4 1 2 4 2 COMPOUND Rate 5 12 13 1415 16 17 19 20 22 23 24 25 26 27 28 29 30 31 34 35 36 37 38 39 40 41 4445 125 g/ha Pre- emergence B. signal- 2 — 10 — 1 10 8 7 — — 8 9 10 5 810 9 8 1 8 6 — — 1 7 9 7 7 8 grass Black- 0 7 9 9 1 10 6 3 9 8 7 8 9 5 59 9 3 0 8 5 10 10 0 6 6 7 2 5 grass Cocklebur 0 6 — 3 0 2 4 0 7 0 6 8 7— 1 1 1 — 0 — 1 2 3 0 7 6 1 0 — Corn 0 2 2 1 0 2 0 2 1 1 1 3 1 0 0 1 2 10 1 1 2 2 0 0 1 1 2 0 Crabgrass 4 10 10 10 1 10 10 9 10 10 10 10 10 9 99 10 9 6 9 10 10 10 1 9 10 10 10 10 Galium 6 6 8 8 3 10 10 7 9 7 8 8 104 7 3 9 7 0 6 8 10 9 0 8 8 6 5 1 Giant 5 10 10 9 3 10 10 9 10 10 10 1010 9 9 10 10 10 8 9 10 10 10 3 10 10 10 10 9 foxtail Morning- 2 10 10 100 10 10 9 10 6 8 10 10 5 5 10 10 10 6 6 9 10 9 0 10 10 3 9 9 gloryNutsedge 0 0 0 0 0 0 0 0 0 0 0 0 1 0 — 1 — 0 0 0 1 — 0 0 — 1 0 0 0 Rape7 9 10 8 5 10 10 8 9 9 10 10 10 8 6 8 10 7 1 9 8 10 10 0 7 9 4 8 4Redroot 9 10 10 9 1 10 10 9 10 10 10 10 10 8 7 10 10 10 5 10 10 10 10 09 8 10 9 9 pigweed Soybean 0 4 3 2 0 4 1 1 2 1 1 7 2 4 1 2 2 3 0 1 2 2 10 3 3 0 5 1 Sugarbeets 8 10 10 10 3 10 10 10 10 9 10 10 10 10 9 10 10 103 10 9 10 10 2 10 10 5 10 10 Velvetleaf 2 10 10 7 0 10 10 7 10 7 8 10 98 7 10 10 7 4 8 9 10 8 1 9 10 0 10 7 Wheat 0 2 2 3 0 2 1 0 3 3 2 3 1 1 10 3 2 0 2 1 2 3 0 1 3 2 20 Wild oats 4 10 9 9 0 10 7 5 8 9 8 9 10 7 6 109 8 0 8 7 10 10 2 9 9 7 5 9 COMPOUND Rate 125 g/ha 46 49 51 52 53 54 5657 Preemergence B. signalgrass 9 10 1 — — — 7 7 Blackgrass 5 10 1 7 2 24 2 Cocklebur 1 2 1 2 0 1 0 0 Corn 1 3 0 5 0 0 2 0 Crabgrass 7 10 6 9 06 10 9 Galium 3 9 7 9 3 6 8 7 Giant foxtail 9 10 9 10 1 3 10 9Morningglory 6 10 5 8 0 7 10 10 Nutsedge 0 1 0 0 — 0 — 0 Rape 6 10 7 9 00 10 9 Redroot pigweed 9 10 7 10 3 6 10 10 Soybean 1 3 0 0 0 0 1 0Sugarbeets 10 10 10 10 3 9 10 9 Velvetleaf 9 10 5 6 0 7 10 7 Wheat 3 1 13 0 0 3 1 Wild oats 7 10 2 9 2 1 10 9 COMPOUND Rate 12 13 14 15 16 17 1920 21 22 23 24 25 27 28 29 30 31 34 35 36 37 38 39 40 41 44 45 46 62g/ha Post- emergence B. signal- — 2 3 3 3 2 1 1 — — 2 3 4 2 6 3 8 2 3 35 5 1 3 3 1 3 4 7 grass Barnyard- 5 4 4 0 4 3 4 4 0 4 2 3 5 2 4 3 4 3 44 7 5 0 4 2 3 3 3 3 grass Black- 4 5 4 1 3 3 2 3 3 6 3 3 5 7 4 2 2 1 3 27 4 1 2 5 1 3 4 3 grass Cocklebur 8 9 9 4 6 8 7 8 7 7 8 7 9 7 7 8 7 8 78 9 9 2 8 8 — — 4 9 Corn 2 2 2 2 2 2 1 2 1 1 1 3 4 2 3 2 3 2 2 2 3 4 1 23 1 4 3 3 Crabgrass 7 8 4 3 9 6 3 6 2 6 4 8 3 3 7 3 6 2 5 5 8 5 0 3 5 35 2 3 Ducksalad 9 2 0 0 8 2 0 2 0 0 1 5 4 3 4 6 0 0 1 2 4 4 0 3 2 2 6 01 Galium 9 9 8 4 10 — 7 8 7 9 — 9 9 10 9 8 10 2 9 9 8 8 1 10 — 8 9 4 9Giant 5 7 2 2 8 6 3 2 2 4 6 7 3 2 5 2 5 2 5 3 7 4 1 6 6 2 6 2 3 foxtailMorning- 10 8 9 2 8 9 2 9 7 8 7 9 — 8 3 8 8 8 8 8 7 1 7 9 3 8 10 7 gloryNutsedge 1 — 1 0 0 0 0 0 0 0 0 0 3 — 0 — 0 0 1 0 2 0 0 0 0 0 — 0 0 Rape10 9 9 6 9 7 6 8 9 10 — 9 9 10 10 8 9 5 9 9 9 9 3 10 10 2 8 8 8 Redroot9 9 8 8 9 9 9 9 4 9 9 10 9 10 9 9 8 8 9 9 8 8 — 10 9 7 9 9 9 pigweedRice 4 3 4 0 6 2 3 4 0 2 1 5 3 1 4 3 4 1 1 1 5 5 0 5 2 1 3 1 3 S. 9 8 30 9 8 7 8 3 2 7 8 8 — 9 4 5 6 5 5 9 8 2 8 6 7 9 8 7 Flatsedge Soybean 66 8 5 7 6 4 7 0 7 3 8 8 7 8 8 9 4 10 8 9 9 1 8 8 0 9 9 7 Sugarbeets 9 98 8 8 9 9 8 6 9 9 10 9 9 9 9 9 8 9 9 9 8 4 10 9 6 10 9 10 Velvetleaf 9 98 3 7 7 3 8 1 9 6 9 9 8 8 8 8 6 9 9 8 8 1 8 7 0 8 7 8 Wheat 1 2 1 0 1 11 1 1 1 1 1 3 1 3 3 1 1 1 1 3 4 0 2 3 1 2 1 3 Wild oats 2 4 3 1 3 2 2 22 6 3 2 5 3 4 3 3 1 2 2 5 4 1 2 4 1 2 3 4 COMPOUND Rate 62 g/ha 49 51 5253 54 56 57 Postemergence B. signalgrass 3 — — — — 2 1 Barnyardgrass 5 04 0 1 6 2 Blackgrass 5 2 5 1 3 3 2 Cocklebur 9 4 5 3 6 6 6 Corn 3 2 3 01 3 2 Crabgrass 9 2 4 0 2 3 3 Ducksalad 6 0 0 0 0 8 3 Galium 9 8 8 7 8 98 Giant foxtail 8 1 5 1 1 7 4 Morningglory 8 3 6 1 6 9 9 Nutsedge 2 0 00 0 0 0 Rape 8 7 7 0 4 9 8 Redroot pigweed 9 9 9 5 6 9 9 Rice 4 0 3 0 07 3 S. Flatsedge 8 0 5 2 5 9 8 Soybean 8 4 5 0 4 5 2 Sugarbeets 9 7 9 69 9 9 Velvetleaf 9 3 6 2 6 6 7 Wheat 2 2 3 0 1 0 1 Wild oats 5 2 4 0 2 31 COMPOUND Rate 12 13 14 15 16 17 19 20 21 22 23 24 25 27 28 29 30 31 3435 36 37 38 40 41 44 45 46 49 62 g/ha Pre- emergence B. signal- — 9 — 09 5 5 — — — 7 9 9 6 9 9 7 0 7 3 — — 0 8 4 5 8 5 10 grass Black- 7 7 6 06 3 2 4 2 3 6 6 8 3 6 5 1 0 3 3 9 10 0 5 3 2 3 3 10 grass Cocklebur 2 51 0 1 3 0 3 0 0 5 1 7 0 — 1 — 0 0 1 2 3 0 6 0 0 0 1 1 Corn 1 1 0 0 1 0 00 0 0 1 1 1 0 1 1 0 0 1 1 1 1 0 1 0 0 0 0 2 Crabgrass 10 10 9 1 10 9 8 82 10 9 10 9 4 8 10 8 2 9 9 10 10 1 9 8 9 8 7 10 Galium 6 7 8 3 10 9 — 80 7 8 7 8 5 3 8 6 0 6 7 8 8 0 8 6 3 0 2 9 Giant 10 10 9 1 10 9 7 8 9 109 10 10 7 10 10 9 4 9 8 10 10 2 9 9 9 4 9 10 foxtail Morning- 7 10 8 010 6 9 8 1 4 4 10 8 5 10 9 7 5 4 5 8 8 0 8 3 8 3 3 10 glory Nutsedge 0 00 0 0 0 0 0 0 0 0 0 1 — 0 0 0 0 0 — 0 — 0 0 0 0 0 0 0 Rape 9 10 8 0 1010 4 9 8 8 10 10 7 5 8 7 3 1 8 8 9 8 0 9 2 8 0 5 10 Redroot 10 10 9 1 1010 9 10 10 8 10 9 3 9 10 8 2 8 10 10 10 0 8 9 9 9 9 10 pigweed Soybean 31 1 0 1 1 0 1 0 1 1 2 1 1 1 1 1 0 0 1 1 1 0 1 0 1 0 0 1 Sugarbeets 10 106 2 10 10 10 10 6 8 10 10 10 9 9 9 8 3 9 8 9 10 0 10 5 10 9 9 10Velvetleaf 9 8 7 0 10 8 3 10 1 5 — 10 9 2 9 10 4 4 8 5 10 7 0 10 0 10 08 10 Wheat 2 1 1 0 2 2 0 1 0 2 1 2 1 1 0 1 1 0 1 1 1 2 0 3 1 2 0 3 1Wild oats 9 9 8 0 10 7 2 5 5 8 5 9 9 5 8 8 6 0 6 4 10 8 0 8 4 4 9 5 10COMPOUND Rate 62 g/ha 51 52 53 54 56 57 Preemergence B. signalgrass — —— — 6 3 Blackgrass 1 1 0 1 2 1 Cocklebur 1 1 0 0 0 0 Corn 0 3 0 0 2 0Crabgrass 6 9 0 4 9 8 Galium 4 5 3 4 8 6 Giant foxtail 7 10 0 1 10 9Morningglory 4 3 0 3 9 3 Nutsedge 0 0 0 0 0 0 Rape 7 6 0 0 10 8 Redrootpigweed 7 9 2 1 10 8 Soybean 0 0 0 0 0 0 Sugarbeets 9 10 2 9 10 7Velvetleaf 5 5 0 2 9 2 Wheat 0 1 0 0 1 0 Wild oats 0 4 0 1 10 4 COMPOUNDRate 12 13 14 16 17 19 22 23 24 25 27 28 34 35 36 37 38 39 40 41 44 4546 49 51 52 53 54 56 31 g/ha Post- emergence B. signal- — 2 2 2 1 1 — 23 3 2 4 2 2 4 4 1 2 3 1 3 3 5 3 — — — — 2 grass Barnyard- 4 3 3 4 2 2 32 2 4 1 3 3 3 5 4 0 4 1 2 3 2 3 4 0 3 0 1 6 grass Black- 2 3 2 3 2 1 3 22 4 3 3 2 1 4 3 0 2 4 1 3 2 2 4 2 4 0 2 2 grass Cocklebur 8 8 7 5 7 6 36 6 9 7 6 7 9 8 8 2 8 8 — 8 4 8 9 4 5 3 6 5 Corn 1 2 2 2 1 1 1 1 2 3 1 22 1 3 3 1 1 3 0 3 3 2 2 2 2 0 1 2 Crabgrass 6 5 4 8 3 2 3 2 7 3 2 3 3 37 5 0 3 3 3 2 2 2 8 2 3 0 1 3 Ducksalad 2 0 0 7 2 0 0 1 1 4 2 1 0 1 3 20 2 1 1 3 2 0 3 0 0 0 0 7 Galium 8 8 8 — — 7 5 9 7 9 8 8 9 — 8 8 0 10 —7 7 4 7 9 8 8 2 8 9 Giant 2 5 2 8 4 2 2 3 6 3 2 3 4 2 6 3 1 5 4 2 3 2 25 0 3 0 1 7 foxtail Morning- 10 — 10 4 8 2 8 3 — 9 2 — — 7 8 7 1 7 8 2 87 3 6 3 6 1 6 8 glory Nutsedge 1 0 0 0 0 0 0 0 0 — 0 0 — 0 — 0 0 0 0 0 00 0 2 0 0 0 0 O Rape 9 8 8 9 7 6 9 7 — 8 9 9 9 9 8 9 2 10 10 1 7 7 8 8 77 0 2 9 Redroot 9 9 8 9 9 8 8 9 10 9 9 9 9 9 6 8 2 9 9 6 8 9 9 9 9 8 4 68 pigweed Rice 4 2 3 5 2 1 0 1 4 2 0 3 1 0 4 4 0 4 2 1 3 0 2 3 0 1 0 0 6S. 8 5 1 9 8 7 1 6 7 6 2 8 1 3 9 6 2 8 4 7 8 8 2 7 0 5 2 1 9 FlatsedgeSoybean 5 6 7 6 6 4 6 3 4 7 6 8 7 7 7 9 1 7 6 0 5 8 6 8 4 5 0 3 5Sugarbeets 7 9 7 8 9 8 9 9 10 8 9 9 9 9 9 8 3 9 9 6 9 9 9 9 7 9 5 8 9Velvetleaf 8 9 7 7 6 3 8 6 8 8 7 8 8 9 7 7 1 6 7 0 6 6 7 8 3 4 0 6 6Wheat 1 1 1 1 1 1 1 1 1 3 1 2 1 1 3 3 0 2 3 1 2 0 3 2 1 2 0 0 0 Wildoats 2 2 3 2 2 1 3 2 2 4 2 3 1 1 4 4 0 2 3 1 1 2 2 4 1 3 0 0 2 COMPOUNDRate 31 g/ha 57 Postemergence B. signalgrass 1 Barnyardgrass 1Blackgrass 1 Cocklebur 6 Corn 1 Crabgrass 2 Ducksalad 2 Galium 8 Giantfoxtail 3 Morningglory 9 Nutsedge 0 Rape 8 Redroot pigweed 9 Rice 3 S.Flatsedge 6 Soybean 2 Sugarbeets 8 Velvetleaf 6 Wheat 1 Wild oats 1COMPOUND Rate 12 13 14 16 17 19 22 23 24 25 27 28 34 35 36 37 38 39 4041 44 45 46 49 51 52 53 54 56 31 g/ha Pre- emergence B. signal- — 9 — 84 2 — 3 9 8 5 9 3 2 — — 0 6 8 3 4 5 4 9 — — — — 4 grass Black- 3 6 3 3 22 1 2 4 4 1 5 2 2 5 8 0 3 4 3 2 3 1 9 0 1 0 0 2 grass Cocklebur 1 1 1 11 0 0 2 0 6 0 — 0 1 1 1 0 1 — 0 0 — 1 1 0 0 0 0 0 Corn 1 0 0 0 0 0 0 0 10 0 0 0 0 1 1 0 0 0 0 0 0 0 1 0 3 0 0 1 Crabgrass 9 9 7 10 9 6 6 8 9 5 37 7 8 10 9 1 9 9 3 5 0 1 10 2 8 0 1 9 Galium 6 6 3 7 6 2 3 8 6 8 — 1 2 37 8 0 3 6 1 2 0 2 9 — 3 0 1 7 Giant 9 9 9 10 9 5 8 8 9 8 5 8 8 6 10 10 110 9 6 8 2 5 10 1 10 0 0 10 foxtail Morning- 7 9 4 10 3 8 2 4 10 6 2 8 22 3 7 0 2 7 2 2 1 1 7 4 2 0 3 3 glory Nutsedge 0 0 0 — 0 0 0 0 0 0 0 0 00 0 — 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 6 9 5 10 10 4 3 9 10 5 2 7 4 3 8 40 3 8 0 2 0 3 9 4 5 0 0 9 Redroot 10 10 8 10 3 9 5 8 9 6 3 8 3 7 8 10 04 8 2 8 5 8 10 7 6 0 1 10 pigweed Soybean 1 1 0 1 1 0 1 1 2 1 0 1 0 1 01 0 2 0 0 0 0 0 1 0 0 0 0 0 Sugarbeets 10 10 6 10 9 10 7 10 10 9 9 9 9 39 9 0 8 9 1 9 2 8 10 6 9 0 9 10 Velvetleaf 8 8 5 8 7 2 4 6 10 7 2 2 6 57 5 0 3 7 0 3 0 2 10 1 2 0 0 5 Wheat 1 1 1 1 1 0 1 1 1 0 0 0 0 0 1 1 0 01 0 0 0 1 1 0 0 0 0 0 Wild oats 8 7 8 9 6 0 6 4 7 7 3 7 3 2 8 4 0 3 6 20 6 3 10 0 3 0 0 9 COMPOUND COMPOUND Rate 31 g/ha 57 Rate 16 g/ha 44Preemergence Postemergence B. signalgrass 2 B. signalgrass 3 Blackgrass1 Barnyardgrass — Cocklebur 0 Blackgrass 2 Corn 0 Cocklebur 8 Crabgrass3 Corn 3 Galium 2 Crabgrass 2 Giant foxtail 8 Ducksalad — Morningglory 2Galium 7 Nutsedge 0 Giant foxtail 2 Rape 7 Morningglory 8 Redrootpigweed 5 Nutsedge 0 Soybean 0 Rape 7 Sugarbeets 4 Redroot pigweed 8Velvetleaf 2 Rice — Wheat 0 S. Flatsedge — Wiid oats 3 Soybean 3Sugarbeets 9 Velvetleaf 6 Wheat 1 Wild oats 1 COMPOUND Morningglory 1Rate 16 g/ha 44 Nutsedge 0 Preemergence Rape 0 B. signalgrass 2 Redrootpigweed 7 Blackgrass 1 Soybean 0 Cocklebur 0 Sugarbeets 7 Corn 0Velvetleaf 0 Crabgrass 3 Wheat 0 Galium 1 Wild oats 0 Giant foxtail 3

Test C

The compounds evaluated in this test were formulated in a non-phytoxicsolvent mixture which included a surfactant and applied to the soilsurface before plant seedlings emerged (preemergence application), towater that covered the soil surface (flood application), and to plantsthat were in the one-to-four leaf stage (postemergence application). Asandy loam soil was used for the preemergence and postemergence tests,while a silt loam soil was used in the flood application. Water depthwas approximately 2.5 cm for the flood application and was maintained atthis level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted ofbarnyardgrass (Echinochloa crus-galli), winter barley (Hordeum vulgare),bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides),chickweed (Stellaria media), cocklebur (Xanthiutn strumarium), corn 1(Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitariasanguinalis), downy brome (Bromus tectorum), giant foxtail (Setariafaberii), johnsongrass (Sorghum halpense), lambsquarters (Chenopodiumalbum), morningglory (Ipomoea hederacea), pigweed (Amaranthusretroflexus), rape (Brassica napus), Italian ryegrass (Loliummultiflonum), soybean (Glycine max), speedwell (Veronica persica), sugarbeet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticumaestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avenafatua). All plant species were planted one day before application of thecompound for the preemergence portion of this test. Plantings of thesespecies were adjusted to produce plants of appropriate size for thepostemergence portion of the test. Plant species in the flood testconsisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis),duck salad (Heteranthera limosa) and barnyardgrass 1 (Echinochloacrus-galli) to the 2 leaf stage for testing.

All plant species were grown using normal greenhouse practices. Visualevaluations of injury expressed on treated plants, when compared tountreated controls, were recorded approximately fourteen to twenty onedays after application of the test compound. Plant response to the testcompound is summarized in Table C, recorded on a 0 to 100 scale where 0is no effect and 100 is complete control. A dash (-) response means notest result.

TABLE C COMPOUND COMPOUND COMPOUND Rate 500 g/ha 6 Rate 500 g/ha 6 Rate250 g/ha 6 POSTEMERGENCE PREEMERGENCE POSTEMERGENCE Barley (winter) 40Barley (winter) 10 Barley (winter) 30 Barnyardgrass 60 Barnyardgrass 85Barnyardgrass 40 Barnyardgrass 1 80 Bedstraw 80 Barnyardgrass 1 50Bedstraw 95 Blackgrass 100 Bedstraw 90 Blackgrass 40 Chickweed 95Blackgrass 35 Chickweed 90 Cocklebur 0 Chickweed 90 Cocklebur 80 Corn 10 Cocklebur 70 Corn 1 30 Cotton 0 Corn 1 30 Cotton 100 Crabgrass 100Cotton 70 Crabgrass 80 Downy brome 70 Crabgrass 70 Downy brome 30 Giantfoxtail 100 Downy brome 20 Ducksalad 50 Italn. ryegrass 50 Ducksalad 30Giant foxtail 50 Johnsongrass 100 Giant foxtail 30 Italn. ryegrass 35Lambsquarter 90 Italn. ryegrass 25 Johnsongrass 70 Morningglory 100Johnsongrass 50 Lambsquarter 100 Rape 100 Lambsquarter 90 Morningglory90 Redroot pigweed 100 Morningglory 90 Rape 100 Soybean 0 Rape 100Redroot pigweed 90 Speedwell 100 Redroot pigweed 90 Rice japonica 20Sugar beet 100 Rice japonica 10 Soybean 80 Velvetleaf 40 Soybean 70Speedwell 100 Wheat 0 Speedwell 100 Sugar beet 90 Wild buckwheat 70Sugar beet 90 Umbrella sedge 80 Wild oat 95 Umbrella sedge 80 Velvetleaf70 Velvetleaf 50 Wheat 25 Wheat 25 Wild buckwheat 95 Wild buckwheat 90Wild oat 60 Wild oat 50 COMPOUND COMPOUND COMPOUND Rate 250 g/ha 6 Rate125 g/ha 6 Rate 125 g/ha 6 PREEMERGENCE POSTEMERGENCE PREEMERGENCEBarley (winter) 0 Barley (winter) 25 Barley (winter) 0 Barnyardgrass 35Barnyardgrass 20 Barnyardgrass 20 Bedstraw 70 Barnyardgrass 1 30Bedstraw 30 Blackgrass 80 Bedstraw 90 Blackgrass 70 Chickweed 95Blackgrass 30 Chickweed 70 Cocklebur 0 Chickweed 90 Cocklebur 0 Corn 1 0Cocklebur 70 Corn 1 0 Cotton 0 Corn 1 25 Cotton 0 Crabgrass 100 Cotton70 Crabgrass 90 Downy brome 20 Crabgrass 60 Downy brome 10 Giant foxtail100 Downy brome 10 Giant foxtail 95 Italn. ryegrass 30 Ducksalad 20Italn. ryegrass 20 Johnsongrass 80 Giant foxtail 30 Johnsongrass 80Lambsquarter 90 Italn. ryegrass 20 Lambsquarter 70 Morningglory 70Johnsongrass 40 Morningglory 35 Rape 80 Lambsquarter 90 Rape 40 Redrootpigweed 100 Morningglory 80 Redroot pigweed 100 Soybean 0 Rape 100Soybean 0 Speedwell 100 Redroot pigweed 90 Speedwell 90 Sugar beet 100Rice japonica 0 Sugar beet 80 Velvetleaf 20 Soybean 60 Velvetleaf 10Wheat 0 Speedwell 100 Wheat 0 Wild buckwheat 70 Sugar beet 90 Wildbuckwheat 40 Wild oat 80 Umbrella sedge 70 Wild oat 50 Velvetleaf 40Wheat 15 Wild buckwheat 80 Wild oat 40 COMPOUND COMPOUND Rate 62 g/ha 6Rate 62 g/ha 6 POSTEMERGENCE PREEMERGENCE Barley (winter) 25 Barley(winter) 0 Barnyardgrass 15 Barnyardgrass 0 Barnyardgrass 1 20 Bedstraw20 Bedstraw 70 Blackgrass 35 Blackgrass 20 Chickweed 50 Chickweed 70Cocklebur 0 Cocklebur 60 Corn 1 0 Corn 1 25 Cotton 0 Cotton 30 Crabgrass35 Crabgrass 40 Downy brome 0 Downybrome 0 Giant foxtail 90 Ducksalad 0Italn. ryegrass 10 Giant foxtail 20 Johnsongrass 20 Italn. ryegrass 15Lambsquarter 40 Johnsongrass 40 Morningglory 0 Lambsquarter 90 Rape 0Morningglory 80 Redroot pigweed 100 Rape 90 Soybean 0 Redroot pigweed 90Speedwell 80 Rice japonica 0 Sugar beet 80 Soybean 50 Velvetleaf 10Speedwell 100 Wheat 0 Sugar beet 90 Wild buckwheat 20 Umbrella sedge 50Wild oat 10 Velvetleaf 30 Wheat 10 Wild buckwheat 80 Wild oat 40

Test D

Compounds evaluated in this test were formulated in a non-phytotoxicsolvent mixture which included a surfactant and applied to plants thatwere grown for various periods of time before treatment (postemergenceapplication). A mixture of sandy loam soil and greenhouse potting mix ina 60:40 ratio was used for the postemergence test.

Plantings of these crops and weed species were adjusted to produceplants of appropriate size for the postemergence test. All plant specieswere grown using normal greenhouse practices. Crop and weed speciesinclude arrowleaf sida (Sida rhombifolia), barnyardgrass (Echinochloacrus-galli), cocklebur (Xanthium strumarium), common ragweed (Ambrosiaelatior), corn 1 (Zea mays), cotton (Gossypium hirsutum), eastern blacknightshade (Solanum ptycanthum), fall panicum (Panicum dichotomiflorum),field bindweed (Convolvulus arvensis), giant foxtail (Setaria faberii),hairy beggarticks (Bidens pilosa), ivyleaf morningglory (Ipomoeahederacea), johnsongrass (Sorghum halepense), ladysthumb smartweed(Polygonum persicaria), lambsquarters (Chenopodium album), largecrabgrass (Digitaria sanguinalis), purple nutsedge (Cyperus rotundus),redroot pigweed (Amaranthus retroflexus), soybean 1 (Glycine max),surinam grass (Brachiaria decumbens), velvetleaf (Abutilon theophrasti)and wild poinsettia (Euphorbia heterophylla).

Treated plants and untreated controls were maintained in a greenhousefor approximately 14 to 21 days, after which all treated plants werecompared to untreated controls and visually evaluated. Plant responseratings, summarized in Table D, were based upon a 0 to 100 scale where 0was no effect and 100 was complete control. A dash response (-) means notest result.

TABLE D COMPOUND Rate 280 g/ha 12 13 14 20 22 25 34 35 49 56 57PREEMERGENCE Arrowleaf sida 100 100 100 100 100 100 95 100 100 100 95Barnyardgrass 100 60 10 80 5 30 100 90 100 40 20 Cocklebur 20 80 30 50 050 35 70 40 25 10 Common ragweed 100 100 100 100 80 100 100 100 100 100— Corn 1 5 5 5 5 0 10 15 10 5 50 10 Cotton 100 100 80 30 20 30 75 80 6050 65 E. blacknightsh 100 100 100 100 100 100 95 100 100 100 100 Fallpanicum 100 100 100 100 100 100 100 100 100 100 85 Field bindweed 100100 100 100 80 100 100 100 100 100 100 Giant foxtail 100 100 100 100 100100 100 100 100 70 100 H. beggarticks 100 100 100 100 70 10 100 95 90 9565 I. morningglory 100 100 80 100 5 100 60 100 100 100 80 Johnsongrass100 50 50 70 50 20 65 75 100 25 15 Ladysthumb 100 — 100 — — 100 100 100— 100 100 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100Large crabgrass 100 100 100 100 100 100 100 100 100 100 100 Purplenutsedge 0 10 0 5 0 0 0 0 5 20 0 Redroot pigweed 100 100 100 100 100 100100 100 100 100 100 Soybean 1 60 50 15 25 20 10 30 20 30 30 0 Surinamgrass 100 85 70 100 55 95 90 85 100 60 40 Velvetleaf 100 90 90 100 70100 100 100 100 100 100 Wild poinsettia 100 100 80 90 50 50 75 100 90100 75 COMPOUND Rate 140 g/ha 12 13 14 16 17 20 22 25 29 34 35 36 37 4049 56 57 PREEMERGENCE Arrowleaf sida 100 100 100 100 90 100 100 95 90 9595 95 95 90 100 100 100 Barnyardgrass 100 40 5 20 20 10 5 10 35 40 25 2040 70 70 40 20 Cocklebur 5 5 5 10 — 50 0 10 — 20 10 0 20 — 40 10 10Common ragweed 85 100 100 20 25 100 55 95 — 100 60 95 90 100 100 100 —Corn 1 5 5 5 35 20 5 0 10 10 10 10 20 10 0 5 35 10 Cotton 75 80 40 15 1595 — 20 70 50 40 60 100 0 55 20 40 E. blacknightsh 100 100 100 95 100100 70 80 95 90 95 100 100 90 100 100 100 Fall panicum 100 100 100 10070 100 90 95 95 100 95 100 100 100 100 90 70 Field bindweed 100 100 10090 95 100 — 100 100 100 100 100 100 95 100 100 75 Giant foxtail 100 100100 50 100 100 90 85 100 100 60 100 100 25 100 100 95 H. beggarticks 80100 85 10 90 100 — 10 35 95 95 95 95 20 50 10 65 I. morningglory 100 10080 60 25 100 5 50 — 60 30 40 75 20 100 85 75 Johnsongrass 100 50 10 2050 30 20 10 85 40 25 20 40 50 55 10 10 Ladysthumb 100 — 100 — — 100 —100 100 95 100 100 100 — — 80 100 Lambsquarters 100 100 100 95 95 100 80100 100 100 100 100 100 100 100 100 100 Large crabgrass 100 100 100 100100 100 100 100 100 100 100 100 100 100 100 50 95 Purple nutsedge 0 0 0— 0 5 0 0 — 0 0 0 0 0 0 0 0 Redroot pigweed 100 100 100 100 100 100 100100 100 100 100 100 100 100 100 100 100 Soybean 1 50 20 5 0 0 15 5 10 1015 15 50 15 0 30 15 0 Surinam grass 100 80 70 30 75 70 20 70 95 80 35 80100 25 100 50 40 Velvetleaf 100 90 90 50 90 70 50 80 95 100 100 100 10085 100 100 100 Wild poinsettia 50 80 10 100 60 60 30 40 65 75 90 100 7060 80 100 40 COMPOUND Rate 10 g/ha 12 13 14 16 17 20 22 25 29 34 35 3637 40 49 56 57 PREEMERGENCE Arrowleaf sida 100 100 100 90 85 100 95 10075 90 80 90 95 90 100 100 95 Barnyardgrass 5 5 5 10 10 5 0 10 10 20 2020 20 25 10 20 10 Cocklebur 0 5 0 10 10 5 0 0 0 10 0 — 20 0 0 0 0 Commonragweed 85 100 95 10 10 80 5 70 — 60 50 100 100 95 60 20 — Corn 1 0 5 010 0 5 0 5 10 10 10 15 0 0 5 25 5 Cotton 5 5 40 10 — 5 0 20 40 25 — 4020 0 55 10 15 E. blacknightsh 100 100 100 95 100 100 50 50 85 90 60 100100 80 100 100 80 Fall panicum 100 100 100 95 60 100 5 80 30 100 100 100100 100 100 70 25 Field bindweed 100 100 100 80 60 100 10 70 70 80 100100 90 60 100 95 75 Giant foxtail 100 100 100 50 95 100 45 20 95 80 10100 10 20 100 80 80 H. beggarticks 80 100 80 10 80 100 50 10 35 70 95 5085 20 45 — 20 I. morningglory 80 5 10 50 10 80 5 25 50 35 30 25 50 20 3040 50 Johnsongrass 50 30 10 20 25 10 5 10 20 15 10 20 25 20 50 0 10Ladysthumb 100 — 100 — — 60 40 50 100 70 100 100 70 — — 80 50Lambsquarters 100 100 100 80 90 100 80 95 — 100 100 100 100 100 100 10080 Large crabgrass 100 100 100 75 100 100 40 60 100 100 — 75 100 80 10040 75 Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot pigweed100 100 100 100 100 100 100 100 100 95 100 100 100 100 100 100 100Soybean 1 5 5 5 0 0 5 0 0 5 10 5 20 10 0 5 0 0 Surinam grass 50 30 10 2025 40 20 40 70 40 20 50 70 20 80 20 30 Velvetleaf 90 80 80 40 70 70 5 8065 90 90 100 100 65 100 100 75 Wild poinsettia 20 60 10 40 10 50 5 25 2040 100 90 50 10 50 20 10 COMPOUND Rate 35 g/ha 12 13 14 16 17 20 22 2529 34 35 36 37 40 49 56 57 PREEMERGENCE Arrowleaf sida 100 90 100 90 10095 50 90 50 90 75 90 85 90 90 100 70 Barnyardgrass 0 0 0 10 10 5 0 10 1010 10 10 10 20 5 10 0 Cocklebur 0 0 0 — — 0 0 — 0 0 0 — 10 0 0 0 —Common ragweed 50 70 40 10 10 30 5 10 — 20 10 100 50 10 50 0 — Corn 1 00 0 0 0 5 0 0 10 5 5 15 0 0 0 0 5 Cotton 5 5 10 5 0 60 0 10 20 15 10 1510 0 10 10 — E. blacknightsh 100 95 100 95 80 100 40 35 70 40 50 95 — 80100 90 80 Fall panicum 100 40 50 50 25 10 — 35 20 70 90 90 80 65 80 20 0Field bindweed 70 100 90 60 25 100 10 65 50 100 95 100 100 20 100 85 65Giant foxtail 100 100 80 25 20 70 5 10 85 20 10 40 10 0 100 10 50 H.beggarticks 30 70 30 10 50 100 50 0 20 20 90 20 10 10 40 0 20 I.morningglory 10 5 5 50 10 60 0 20 10 20 30 20 20 10 10 20 20Johnsongrass 5 10 0 10 10 10 0 10 10 10 10 10 10 20 5 0 5 Ladysthumb 100— 100 — — 60 — 40 65 60 100 90 — — — 20 — Lambsquarters 100 100 100 2080 100 60 85 95 95 95 100 100 20 100 100 20 Large crabgrass 100 100 10050 75 100 40 50 85 100 100 50 25 50 80 30 25 Purple nutsedge 0 0 0 0 0 00 0 0 0 0 0 0 0 0 0 0 Redroot pigweed 100 100 100 50 100 100 50 80 10090 50 90 100 80 100 95 95 Soybean 1 5 0 5 0 0 5 0 — 0 5 0 10 5 0 5 0 0Surinam grass 45 10 5 10 10 5 5 20 65 20 10 30 20 10 10 20 15 Velvetleaf75 50 20 10 40 50 0 50 50 90 80 75 60 20 60 100 40 Wild poinsettia 15 305 10 — 30 0 10 10 20 25 70 40 10 10 10 10 COMPOUND Rate 17 g/ha 12 16 1720 29 36 37 40 PREEMERGENCE Arrowleaf sida 90 80 90 25 25 80 80 70Barnyardgrass 0 10 0 10 5 10 5 10 Cocklebur 0 — 0 0 0 0 0 Common ragweed10 10 0 25 — 30 10 10 Corn 1 5 0 0 0 5 10 0 0 Cotton 10 0 0 10 20 5 10 0E. blacknightsh 25 100 25 80 70 50 75 80 Fall panicum 20 25 10 20 10 7050 50 Field bindweed 65 35 20 50 20 80 70 20 Giant foxtail 20 20 20 1030 10 10 0 H. beggarsticks 0 0 10 10 10 0 10 0 I. morningglory 10 40 1020 10 10 10 10 Johnsongrass 10 10 0 10 5 5 10 0 Ladysthumb 80 — — 15 1010 50 — Lambsquarters 100 — 10 70 20 50 95 10 Large crabgrass 40 50 2040 60 30 25 25 Purple nutsedge 0 0 0 0 0 0 0 0 Redroot pigweed 100 — 6565 95 90 65 70 Soybean 1 5 0 0 0 0 0 5 0 Surinam grass 20 10 10 10 25 1010 10 Velvetleaf 30 0 10 50 — 50 50 10 Wild poinsettia 10 0 0 10 0 20 100

Test E

Compounds evaluated in this test were formulated in a non-phytotoxicsolvent mixture which included a surfactant and applied to the soilsurface before plant seedlings emerged (preemergence application) and toplants that were grown for various periods of time before treatment(postemergence application). A sandy loam soil was used for thepreemergence test while a mixture of sandy loam soil and greenhousepotting mix in a 60:40 ratio was used for the postemergence test. Testcompounds were applied within approximately one day after planting seedsfor the preemergence test, and 13 days after the last postemergenceplanting.

Plantings of these crops and weed species were adjusted to produceplants of appropriate size for the postemergence test. All plant specieswere grown using normal greenhouse practices. Crop and weed speciesinclude alexandergrass (Brachiaria plantaginea), black nightshade(Solanum americanum), apple-of-Peru (Nicandra physaloides), arrowleafsida (Sida rhombzfolia), Brazilian sicklepod (Cassia tora Brazilian),Brazilian signalgrass (Brachiaria decumbens), bristly starbur(Acanthospermum hispidum), capim-colchao (Digitaria horizontalis), corn(Zea mays), soybean 1 (Glycine max cv. Cristalina), hairy beggarticks(Bidens pilosa), slender amaranth (Amaranthus viridis), southern sandur(Cenchrus echinatus), tall morningglory (Ipomoea purpurea), tropicalspiderwort (Commelina benghalensis), Soybean 2 (Glycine max cv. W20),Soybean 3 (Glycine max cv. W4-4) and wild pointsettia (Eupohorbiaheterophylla).

Treated plants and untreated controls were maintained in a greenhousefor approximately 13 days, after which all treated plants were comparedto untreated controls and visually evaluated. Plant response ratings,summarized in Table E, are based upon a 0 to 100 scale where 0 is noeffect and 100 is complete control. A dash response (-) means no testresult.

TABLE E COMPOUND Rate 140 g/ha 12 13 14 20 22 49 PREEMERGENCEAlexandergrass 80 70 60 85 60 10 Apple-of-Peru 100 100 90 100 90 5Arrowleaf sida 100 100 100 100 90 80 B. Signalgrass 100 70 50 70 80 10Blk nightshade 100 100 100 100 100 90 Braz sicklepod 50 80 70 90 60 0Bristly starbur 100 60 90 100 100 0 Capim-Colch 100 100 90 100 60 70Corn 10 5 5 5 5 20 H. beggarticks 0 100 90 100 100 0 Morningglory 80 7070 40 60 40 S. amaranth 100 100 100 100 100 100 S. sandbur 80 75 50 5060 5 Soybean 1 70 40 35 25 60 5 Soybean 2 50 10 10 60 45 5 Soybean 3 8020 10 10 70 10 Tr. Spiderwort 100 100 85 95 90 0 Wild poinsettia 100 9050 60 70 100 COMPOUND Rate 70 g/ha 12 13 14 20 22 49 PREEMERGENCEAlexandergrass 60 40 30 10 60 0 Apple-of-Peru 100 90 70 100 80 0Arrowleaf sida 100 100 90 100 — 80 B. Signalgrass 60 40 20 50 40 0 Blknightshade 100 100 100 100 90 80 Braz sicklepod 40 10 5 40 — 0 Bristlystarbur 5 — 40 100 40 0 Capim-Colch 90 90 90 100 60 70 Corn 5 5 0 0 0 5H. beggarticks 0 100 10 90 100 0 Morningglory 40 50 10 40 50 5 S.amaranth 100 100 100 100 100 100 S. sandbur 75 40 5 30 — 0 Soybean 1 3530 15 25 50 0 Soybean 2 40 5 10 15 5 5 Soybean 3 50 15 5 10 10 0 Tr.Spiderwort 80 100 60 95 90 0 Wild poinsettia 100 50 10 30 — 5 COMPOUNDRate 35 g/ha 12 13 14 20 22 49 PREEMERGENCE Alexandergrass 60 30 20 10 00 Apple-of-Peru 10 80 5 90 80 0 Arrowleaf sida 90 80 85 90 80 0 B.Signalgrass 30 5 5 5 10 0 Blk nightshade 100 100 90 90 90 50 Brazsicklepod 0 0 0 5 20 0 Bristly starbur 5 0 0 90 — — Capim-Colch 90 80 5090 10 60 Corn 0 0 0 0 0 0 H. beggarticks 0 50 0 100 0 0 Morningglory 550 5 10 50 0 S. amaranth 100 100 90 100 85 80 S. sandbur 20 5 0 10 0 0Soybean 1 10 10 5 10 10 0 Soybean 2 5 5 5 15 5 0 Soybean 3 10 10 5 5 5 0Tr. Spiderwort 20 10 0 20 40 0 Wild poinsettia 5 5 — 30 40 0 COMPOUNDRate 17 g/ha 12 13 14 20 22 49 PREEMERGENCE Alexandergrass 5 0 0 0 0 0Apple-of-Peru — 0 0 85 80 0 Arrowleaf sida 85 70 80 70 50 0 B.Signalgrass 5 0 0 0 — 0 Blk nightshade 85 85 80 90 80 10 Braz sicklepod— 0 0 5 20 0 Bristly starbur — 0 0 85 20 0 Capim-Colch 50 40 20 80 — 0Corn 0 0 0 0 0 0 H. beggarticks 0 — 0 0 0 0 Morningglory 0 0 0 5 5 0 S.amaranth 100 60 90 60 80 70 S. sandbur 0 0 0 0 0 0 Soybean 1 5 5 0 10 100 Soybean 2 5 5 0 5 5 0 Soybean 3 0 10 0 5 5 0 Tr. Spiderwort 5 0 0 0 —0 Wild poinsettia 5 5 5 10 40 0

TEST F

Seeds, tubers, or plant parts of alexandergrass (Brachiariaplantaginea), broadleaf signalgrass (Brachiaria decumbens), bermudagrass(Cynodon dactylon), common purslane (Portulaca oleracea), common ragweed(Ambrosia elatior), common groundsel (Senecio vulgaris), dallisgrass(Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicummaximum), itchgrass (Rottboellia exaltata), johnson grass (Sorghumhalepense), large crabgrass (Digitaria sanguinalis), pitted morningglory(Ipomoea lacunosa), peanuts (Arachis hypogaea), purple nutsedge (Cyperusrotundus), sandbur (Cenchrus echinatus), sourgrass (Trichachneinsularis), Spanishneedles (Bidens bipinnata), sugarcane (Sacchanimofficinarum), surinam grass (Brachiaria decumbens) and tall mallow(Malva sylvestris) were planted into greenhouse pots of flats containinggreenhouse planting medium. Plant species were grown grown in separatepots or individual compartments. Preemergence applications were madewithin one day of planting the seed or plant part. Postemergenceapplications were applied when the plants were in the two to four leafstage (three to twenty cm).

Test chemicals were formulated in a non-phytotoxic solvent mixture whichincluded a surfactant and applied preemergence and postemergeilce to theplants. Untreated control plants and treated plants were placed in thegreenhouse and visually evaluated for injuly 13 to 21 days afterherbicide application. Plant response ratings, summarized in Table F,are based on a 0 to 100 scale where 0 is no injury and 100 is completecontrol. A dash (-) response means no test result.

TABLE F COMPOUND COMPOUND Rate 1000 g/ha 13 Rate 500 g/ha 12 13 19 20POST DIRECTED PREEMERGENCE Citrus 0 A. bluegrass — — — — Alexandergrass100 — 100 100 Arrowleaf sida — — — — COMPOUND B. signalgrass — — — —Rate 500 g/ha 12 13 19 20 Barnyardgrass — — — — POSTEMERGENCEBermudagrass 100 — 100 100 Alexandergrass 100 — 100 90 C. purslane 100 —100 100 B. signalgrass — — — — C. ragweed 100 — 100 100 Bermudagrass 50— 10 40 Com. chickweed — — — — C. purslane 75 — 75 70 Com. groundsel 100— 100 100 C. ragweed 100 — 75 90 Cotton — — — — Com. groundsel 40 — 30100 Dallisgrass 100 — 100 100 Dallisgrass — — 65 85 Goosegrass 100 — 100100 Goosegrass 90 — 75 90 Green foxtail — — — — Guineagrass 95 — 70 85Guineagrass — — — — Itchgrass 90 — 65 75 Itchgrass 98 — 90 100Johnsongrass 90 — 75 90 Johnsongrass 100 — 70 100 Large crabgrass 80 —70 85 Kochia — — — — P. morninglory 90 — 75 90 Large crabgrass 100 — 100100 Peanuts — — — — Leafy spurge — — — — Purple nutsedge 0 — 0 5 P.morninglory 100 — 80 100 Sandbur — — 10 70 Peanuts — — — — Sourgrass 40— 75 60 Purple nutsedge 10 — 0 0 Spanishneedles 20 — 30 50 Quackgrass —— — Sugarcane — 20 — — Sandbur 100 — 50 100 Surinam grass 90 — 75 80Sourgrass 100 — 100 100 Tall Mallow 100 — 95 100 Spanishneedles 100 —100 100 Sugarcane — 100 — — Surinam grass 100 — 98 100 Tall Mallow 100 —100 100 COMPOUND Rate 250 g/ha 12 13 16 17 19 20 23 25 35 36 37 49 50 56POSTEMERGENCE Alexandergrass 90 75 85 40 30 50 25 80 30 95 90 10 20 80B. signalgrass — 80 — — — — — — — — — — — — Bermudagrass 40 10 20 10 1040 10 30 30 40 40 0 20 10 C. purslane 75 100 30 20 75 70 25 75 70 65 7010 25 75 C. ragweed 75 65 80 75 — 70 30 50 100 65 50 70 45 40 Com.groundsel 40 — 80 100 0 90 70 80 60 80 85 10 70 95 Dallisgrass 90 10 8090 65 75 65 80 95 80 95 30 80 75 Goosegrass 90 20 80 90 — 90 10 90 95 9090 10 30 80 Guineagrass 80 95 70 70 20 75 75 65 40 80 80 50 40 30Itchgrass 90 40 85 80 20 65 10 40 75 65 60 60 85 40 Johnsongrass 85 4085 30 75 75 10 35 65 40 75 20 65 20 Large crabgrass 80 95 85 85 35 75 6080 75 90 85 40 20 70 P. morninglory 95 95 85 80 65 80 40 85 90 90 90 5075 80 Peanuts — 75 — — — — — — — — — — — — Purple nutsedge 0 20 40 10 05 5 5 0 10 5 0 20 40 Sandbur 60 20 0 40 5 30 10 20 20 20 65 0 0 0Sourgrass 40 35 20 10 30 60 10 30 20 60 30 40 10 40 Spanishneedles 20 —20 20 10 40 10 60 35 70 65 10 10 40 Sugarcane — 25 — — — — — — — — — — —— Surinam grass 75 85 70 40 75 50 10 30 — 40 75 10 10 20 Tall Mallow 100— 85 85 98 100 45 90 100 90 85 65 75 85 COMPOUND Rate 250 g/ha 12 13 1617 19 20 23 25 35 36 37 49 50 56 PREEMERGENCE A. bluegrass 100 — — — —100 — — — 100 100 — — 100 Alexandergrass 100 100 100 80 65 100 95 100100 100 100 30 30 — Arrowleaf sida 100 100 — — — 100 — — — 100 100 — —100 B. signalgrass 100 100 — — — 100 — — — 100 100 20 — 100Barnyardgrass 100 98 — — — 100 — — — 100 100 — — 90 Bermudagrass 100 100100 100 100 100 100 100 100 100 100 98 100 — C. purslane 100 100 100 100100 100 100 100 100 100 100 100 100 100 C. ragweed 100 100 100 100 100100 100 100 100 100 100 95 100 — Com. chickweed 100 100 — — — 100 — — —100 100 — — 100 Com. groundsel 100 100 100 100 75 100 100 100 100 100100 0 100 — Cotton — 90 — — — — — — — — — 0 — — Dallisgrass 100 100 100100 95 100 100 100 100 100 100 70 95 — Goosegrass 100 100 100 100 100100 100 100 100 100 100 98 100 100 Green foxtail 100 100 — — — 100 — — —100 100 — — 100 Guineagrass — 100 100 100 — — 100 100 — 100 100 100 50 —Itchgrass 100 60 90 60 80 100 75 75 95 85 95 30 65 — Johnsongrass 100 7080 100 50 98 65 15 100 100 100 20 60 — Kochia 100 100 — — — 100 — — —100 100 — — 100 Large crabgrass 100 100 100 100 100 100 100 100 100 100100 98 90 100 Leafy spurge 100 100 — — — 100 — — — 100 100 — — 100 P.morninglory 100 95 100 90 80 100 90 100 100 98 98 10 100 100 Peanuts —10 — — — — — — — — — 0 — — Purple nutsedge 0 20 20 0 10 0 0 20 0 0 0 020 75 Quackgrass 100 98 — — — 100 — — — 100 100 — — 100 Sandbur 100 80100 50 30 160 65 50 90 100 100 0 20 80 Sourgrass 100 100 100 100 100 100100 100 100 100 100 100 100 — Spanishneedles 100 100 90 100 50 100 100100 100 100 100 30 100 — Sugarcane — 15 — — — — — — — — — — — — Surinamgrass 100 100 100 98 90 100 85 100 100 100 100 10 20 75 Tall Mallow 100100 100 100 100 100 100 100 100 100 100 100 98 — COMPOUND Rate 125 g/ha12 13 19 20 25 35 36 37 49 56 POSTEMERGENCE Alexandergrass 80 20 30 2020 30 30 50 40 30 B. signalgrass — 50 — — — — — — 20 Bermudagrass 30 1010 30 10 30 20 20 10 10 C. purslane 65 90 75 70 60 70 65 60 100 60 C.ragweed 75 100 40 70 50 65 35 35 100 30 Com. groundsel 35 — 0 80 30 6075 75 — 80 Dallisgrass 80 10 65 40 20 50 75 75 0 70 Goosegrass 90 0 — 7590 65 60 85 30 70 Guineagrass 80 30 10 30 40 20 80 75 50 40 Itchgrass 6020 20 65 10 75 35 35 20 10 Johnsongrass 75 35 40 75 10 65 35 40 35 10Large crabgrass 80 60 35 75 80 30 30 75 65 70 P. morninglory 95 100 5080 85 90 85 85 85 85 Peanuts — 50 — — — — — — 70 — Purple nutsedge 0 100 0 0 0 0 5 0 0 Sandbur 40 0 0 20 20 10 5 40 0 0 Sourgrass 20 20 30 3530 20 35 30 20 35 Spanishneedles 20 — 10 40 40 5 40 50 — 30 Sugarcane —20 — — — — — — — — Surinam grass 65 65 30 35 30 70 35 35 65 10 TallMallow 100 — 98 100 80 100 90 85 — 98 COMPOUND Rate 125 g/ha 12 13 16 1719 20 23 25 35 36 37 49 50 56 PREEMERGENCE A. bluegrass 100 — — — — 100— — — 100 100 — — 100 Alexandergrass 100 75 100 50 0 100 75 80 100 100100 90 10 — Arrowleaf sida 100 95 — — — 100 — — — 100 100 — — 100 B.signalgrass 100 90 — — — 100 — — — 100 100 100 — 100 Barnyardgrass 90 80— — — 95 — — — 100 100 — — 80 Bermudagrass 100 100 100 100 98 100 100100 100 100 100 100 100 — C. purslane 100 100 100 100 100 100 100 100100 100 100 100 100 100 C. ragweed 100 100 100 100 65 100 100 100 100100 100 100 100 — Com. chickweed 100 100 — — — 100 — — — 100 100 — — 100Com. groundsel 100 100 98 100 75 100 100 100 100 100 100 0 100 — Cotton— 40 — — — — — — — — — 40 — — Dallisgrass 100 100 100 100 80 100 100 100100 100 100 100 70 — Goosegrass 100 100 100 100 100 100 100 100 100 100100 100 100 100 Green foxtail 100 100 — — — 100 — — — 100 100 — — 100Guineagrass — 100 100 98 — — 100 100 — 100 100 100 20 — Itchgrass 95 2060 40 30 100 40 5 70 75 80 65 40 — Johnsongrass 100 0 40 100 20 80 30 550 30 100 50 30 — Kochia 100 100 — — — 100 — — — 100 100 — — 100 Largecrabgrass 100 100 100 100 100 100 100 100 100 100 100 100 90 100 Leafyspurge 100 100 — — — 100 — — — 100 100 — — 100 P. morninglory 100 75 10090 80 100 98 100 100 100 98 80 80 100 Peanuts — 10 — — — — — — — — — 0 —— Purple nutsedge 0 0 20 0 10 0 0 0 0 0 0 30 — 10 Quackgrass 100 95 — —— 100 — — — 100 100 — — 100 Sandbur 100 10 100 10 10 100 40 10 75 90 6040 0 60 Sourgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 —Spanishneedles 90 100 70 80 30 100 80 100 100 100 100 0 50 — Sugarcane —15 — — — — — — — — — — — — Surinam grass 100 75 100 40 10 100 85 100 95100 100 100 0 65 Tall Mallow 100 100 100 100 100 100 100 100 100 100 100100 100 — COMPOUND Rate 64 g/ha 12 13 19 20 35 49 POSTEMERGENCEAlexandergrass 90 20 20 — 10 10 B. signalgrass — 20 — — — 10Bermudagrass 20 10 10 20 20 10 C. purslane 65 90 50 70 70 100 C. ragweed50 100 30 50 — 10 Com. groundsel 20 — 0 65 — — Dallisgrass 35 10 20 2020 0 Goosegrass 80 0 75 75 65 30 Guineagrass 30 10 10 30 — 35 Itchgrass40 10 10 20 75 20 Johnsongrass 40 5 20 65 35 35 Large crabgrass 50 30 1050 20 20 P. morninglory 90 95 60 80 80 85 Peanuts — 65 — — — 50 Purplenutsedge 0 10 0 0 0 0 Sandbur 0 0 0 10 0 0 Sourgrass 10 10 30 20 — 20Spanishneedles 5 — 10 50 5 — Sugarcane — 20 — — — — Surinam grass 65 030 35 70 35 Tall Mallow 100 — 95 100 100 — COMPOUND Rate 64 g/ha 12 1316 17 19 20 23 25 35 36 37 49 50 56 PREEMERGENCE A. bluegrass 100 — — —— 95 — — — 100 100 — — 98 Alexandergrass 100 70 80 10 0 100 30 50 65 10080 75 0 100 Arrowleaf sida 100 95 — — — 100 — — — 100 100 — — 100 B.signalgrass 100 65 — — — 98 — — — 100 100 90 — 85 Barnyardgrass 35 65 —— — 25 — — — 80 98 — — 40 Bermudagrass 100 98 100 100 90 100 100 100 100100 100 100 95 100 C. purslane 100 100 100 100 100 100 100 100 100 100100 100 100 100 C. ragweed 100 100 98 95 0 98 98 100 100 100 100 100 100100 Com. chickweed 100 100 — — — 100 — — — 98 100 — — 100 Com. groundsel100 100 100 100 0 100 100 100 100 100 100 0 95 95 Cotton — 40 — — — — —— — — — 15 — — Dallisgrass 100 90 100 60 20 100 80 — 100 100 100 98 50100 Goosegrass 100 100 100 90 100 100 100 100 100 100 100 100 95 100Green foxtail 100 100 — — — 100 — — 100 100 — — 100 Guineagrass — 100100 90 — — 80 80 — 100 100 100 20 100 Itchgrass 100 35 35 10 — 75 20 5 510 80 50 20 10 Johnsongrass 40 20 10 100 0 40 30 5 20 5 10 35 10 5Kochia 100 100 — — — 100 — — — 100 100 — — 100 Large crabgrass 100 100100 90 100 100 100 100 100 100 100 100 30 100 Leafy spurge 100 100 — — —100 — — — 100 100 — — 100 P. morninglory 95 60 100 80 35 100 60 90 10095 100 70 80 100 Peanuts — 5 — — — — — — — — — 0 — — Purple nutsedge 020 0 0 0 0 0 0 0 0 0 35 0 20 Quackgrass 98 50 — — — 100 — — — 100 100 —— 90 Sandbur 35 20 50 10 0 75 20 5 20 30 60 35 0 10 Sourgrass 100 100100 95 0 100 100 100 100 100 100 100 98 100 Spanishneedles 75 60 50 7030 100 70 100 100 100 100 0 20 80 Sugarcane — 10 — — — — — — — — — — — —Surinam grass 85 75 90 65 10 90 20 80 60 100 100 80 0 0 Tall Mallow 100100 100 100 100 100 98 100 100 100 100 100 100 100 COMPOUND COMPOUNDRate 32 g/ha 12 19 20 Rate 32 g/ha 12 19 20 POSTEMERGENCE POSTEMERGENCEAlexandergrass 40 0 20 Johnsongrass 20 20 65 B. signalgrass — — — Largecrabgrass 20 10 40 Bermudagrass 10 0 20 P. morninglory 65 60 80 C.purslane 65 50 70 Peanuts — — — C. ragweed 50 30 50 Purpie nutsedge 0 00 Com. groundsel 20 0 0 Sandbur 0 0 5 Dallisgrass 35 20 10 Sourgrass 1020 20 Goosegrass 75 70 75 Spanishneedles 5 10 35 Guineagrass 20 0 10Sugarcane — — — Itchgrass 20 5 20 Surinam grass 65 30 20 Tall Mallow 9075 80 COMPOUND Rate 32 g/ha 12 13 16 17 19 20 23 25 36 37 49 50 56PREEMERGENCE A. bluegrass 98 — — — — 100 — — 100 80 — — 80Alexandergrass 75 10 30 0 0 50 10 35 75 — 0 0 35 Arrowleaf sida 100 90 —— — 100 — — 100 100 — — 100 B. signalgrass 85 0 — — — 80 — — 100 100 0 —75 Barnyardgrass 5 20 — — — 10 — — 30 20 — — 35 Bermudagrass 100 60 10090 60 100 100 100 100 100 10 75 100 C. purslane 100 100 100 100 100 100100 100 100 100 80 100 100 C. ragweed 100 60 90 90 0 98 98 90 75 100 9098 90 Com. chickweed 95 65 — — — 100 — — 100 98 — — 100 Com. groundsel98 100 75 100 0 100 100 100 100 100 0 75 50 Cotton — 0 — — — — — — — — 0— — Dallisgrass 80 60 100 70 0 98 30 80 90 100 0 20 65 Goosegrass 100 98100 80 0 100 100 100 100 100 80 50 100 Green foxtail 100 100 — — — 100 —— 100 100 — — 100 Guineagrass — 80 90 60 — — 70 70 75 100 20 — 85Itchgrass 40 0 20 20 — 75 20 5 0 65 0 20 — Johnsongrass 30 0 10 100 0 —10 5 5 10 0 10 5 Kochia 100 98 — — — 100 — — 100 100 — — 100 Largecrabgrass 100 30 100 80 0 100 35 80 100 100 0 20 85 Leafy spurge 100 75— — — 100 — — 100 100 — — 100 P. morninglory 100 10 80 0 35 100 40 10025 100 0 65 70 Peanuts — 0 — — — — — — — — 0 — — Purple nutsedge 0 0 0 00 0 0 0 0 0 0 0 0 Quackgrass 50 0 — — — 35 — — 95 90 — — 65 Sandbur 35 010 0 0 0 0 0 0 60 0 0 0 Sourgrass 98 98 100 90 0 100 90 100 100 100 4098 100 Spanishneedles 60 0 50 70 20 100 70 40 100 100 0 0 5 Sugarcane —10 — — — — — — — — — — — Surinam grass 75 10 35 20 10 50 10 40 10 100 00 0 Tall Mallow 100 98 100 100 100 100 98 100 98 100 98 98 100 COMPOUNDRate 16 g/ha 12 13 16 17 20 23 25 36 37 49 50 56 PREEMERGENCE A.bluegrass 35 — — — 50 — — 80 80 — — 20 Alexandergrass — 0 0 0 — 0 10 — —0 0 0 Arrowleaf sida 95 75 — — 100 — — 98 98 — — 95 B. signalgrass 20 0— — 20 — — 90 90 0 — 5 Barnyardgrass 5 20 — — 0 — — 20 10 — — 5Bermudagrass — 40 100 75 — 80 10 — — 0 70 98 C. purslane 100 98 100 100100 100 100 100 100 40 95 100 C. ragweed — — 65 — — 90 0 — — 25 0 95Com. chickweed 95 20 — — 80 — — 98 80 — — 80 Com. groundsel — 100 50 95— 100 95 — — 0 20 0 Cotton — 0 — — — — — — — 0 — — Dallisgrass — 40 0 10— 20 10 — — 0 0 5 Goosegrass 100 60 100 5 100 40 75 100 100 0 10 80Green foxtail 100 80 — — 80 — — 100 75 — — 25 Guineagrass — 60 90 40 —30 0 — — 0 0 100 Itchgrass — 0 10 20 — 20 0 — — 0 0 10 Johnsongrass — 00 50 — 0 0 — — 0 10 5 Kochia 90 98 — — 98 — — 100 100 — — 100 Largecrabgrass 90 30 70 5 75 5 35 100 50 0 0 35 Leafy spurge 80 75 — — 90 — —90 100 — — 100 P. morninglory 20 0 50 0 20 20 60 60 30 0 30 70 Peanuts —— — — — — — — — 0 — — Purple nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 Quackgrass10 0 — — 10 — — 80 50 — — 0 Sandbur 0 0 0 0 0 0 0 5 20 0 0 0 Sourgrass —30 100 0 — 70 85 — — 0 50 100 Spanishneedles — 0 0 20 — 0 30 — — 0 0 5Sugarcane — — — — — — — — — — — — Surinam grass 30 10 35 — 30 0 5 10 700 0 0 Tall Mallow — 98 100 90 — 80 95 — — 0 98 98 COMPOUND COMPOUND Rate8 g/ha 12 20 36 37 56 Rate 8 g/ha 12 20 36 37 56 PREEMERGENCEPREEMERGENCE A. bluegrass 0 40 40 80 20 Itchgrass — — — — 0Alexandergrass — — — — 0 Johnsongrass — — — — 0 Arrowleaf sida 0 85 9590 95 Kochia 65 100 98 100 90 B. signalgrass 10 0 35 70 5 Largecrabgrass 30 0 65 50 35 Barnyardgrass 0 0 20 10 0 Leafy spurge 65 75 7080 80 Bermudagrass — — — — 25 P. morninglory 0 20 60 — 30 C. purslane 75100 100 100 85 Peanuts — — — — — C. ragweed — — — — 75 Purple nutsedge 00 0 0 0 Com. chickweed 20 60 20 70 0 Quackgrass 10 0 55 10 0 Com.groundsel — — — — — Sandbur 0 0 0 0 0 Cotton — — — — — Sourgrass — — — —50 Dallisgrass — — — — 0 Spanishneedles — — — — 0 Goosegrass 65 10 — 10065 Sugarcane — — — — — Green foxtail 95 50 85 — — Surinam grass 0 0 1065 0 Guineagrass — — — — 60 Tall Mallow — — — — 100

Test G

Compounds evaluated in this test were formulated in a non-phytotoxicsolvent mixture which included a surfactant and applied to plants thatwere in the 1- to 4-leaf stage (postemergence application). A mixture ofsandy loam soil and greenhouse potting mix in a 60:40 ratio was used forthe postemergence test.

Plantings of these crops and weed species were adjusted to produceplants of appropriate size for the postemergence test. All plant specieswere grown using normal greenhouse practices. Crop and weed speciesinclude alfalfa (Medicago sativa), annual bluegrass (Poa annua),blackgrass 2 (Alopecurus myosuroides), black nightshade (Solanum nigra),chickweed (Stellaria media), common poppy (Papaver rhoeas), deadnettle(Lantium amplexicaule), downy brome (Bromus tectorum), field violet(Viola arvensis), galium 2 (Galium aparine), green foxtail (Setariaviridis), ryegrass (Lolium multiflorum), jointed goatgrass (Aegilopscylindrica), kochia (Kochia scoparia), larfibsquarters (Chlenopoditimalbum), lentil (Lens culinaris), littleseed canarygrass (Phialarisminor), pea (Pisuni salivum), potato (Solanum tuberosum), rape I(Brassica napus), redroot pigweed (Amaranthus retroflexus), Russianthistle (Salsola kali), scentless chamomile (Matricaria inodora), springbarley (Hordeum vulgare), sugar beet (Beta vulgaris), sunflower(Helianithus annuus), ivyleaf speedwell (Veronica hederaefolia), springwheat (Triticum aestivum), winter wheat (Triticum aestivum), wildbuckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wildoat 1 (Avena fatua), windgrass (Apera spica-venti) and winter barley(Hordeum vulgare). Treated plants and untreated controls were maintainedin a greenhouse for approximately 21 to 28 days, after which all treatedplants were compared to untreated controls and visually evaluated. Plantresponse ratings, summarized in Table G, are based upon a 0 to 100 scalewhere 0 is no effect and 100 is complete control. A dash response (-)means no test result.

TABLE G COMPOUND COMPOUND Rate 250 g/ha 20 24 Rate 250 g/ha 20 25 29 3637 57 POSTEMERGENCE PREEMERGENCE Annual bluegras 60 50 Alfalfa — — — — —— Barley (winter) 50 10 Annual bluegras 100 90 85 85 100 75 Blackgrass(2) 30 30 Barley (winter) 30 10 30 20 10 5 Blk nightshade 95 100Blackgrass (2) 90 70 50 100 70 30 Chickweed 90 65 Blk nightshade 100 100100 100 100 100 Common poppy 100 70 Chickweed 85 85 100 100 100 70Deadnettle 95 70 Common poppy 100 100 100 100 100 100 Downy brome 40 20Deadnettle 70 70 100 85 70 — Field violet 100 100 Downy brome 100 85 20100 100 30 Galium (2) 60 65 Field violet 100 100 85 50 100 60 Greenfoxtail 85 95 Galium (2) 100 100 85 100 100 100 I. Ryegrass 20 20 Greenfoxtail 100 100 100 100 100 100 Jointed goatgra 30 30 I. Ryegrass 75 6565 100 100 10 Kochia 75 70 Jointed goatgra 65 40 20 90 65 10Lambsquarters 100 75 Kochia 85 100 100 100 100 100 LS canarygrass 65 30Lambsquarters 75 85 70 85 70 70 Rape (1) 100 100 Lentil — — — — — —Redroot pigweed 75 70 LS canarygrass 100 65 85 75 70 70 Russian thistie80 65 Pea — — — — — — Scentless chamo 100 75 Potato — — — — — — SpringBarley 30 10 Rape (1) 90 100 85 85 75 100 Sugar beet 100 100 Redrootpigweed 100 85 100 100 85 75 Sunflower 60 60 Russian thistle 100 85 100100 100 60 Veronica hedera — 70 Scentless chamo 85 70 85 85 70 75 Wheat(spring) 30 15 Sorghum — — — — — — Wheat (winter) 20 10 Spring Barley 2010 10 20 20 10 Wild buckwheat 55 70 Sugar beet 100 100 100 100 100 70Wild mustard 100 100 Sunflower 30 80 35 60 80 10 Wild oat (1) 45 30Veronica hedera 100 100 100 100 100 — Windgrass 60 60 Wheat (spring) 3010 10 40 30 10 Wheat (winter) 20 10 10 20 30 5 Wild buckwheat 100 90 100100 100 100 Wiid mustard 100 100 100 100 100 100 Wild oat (1) 90 60 7585 90 20 Windgrass 100 100 85 100 70 100 COMPOUND Rate 125 g/ha 6 13 1420 21 22 49 51 56 POSTEMERGENCE Annual bluegras 20 50 60 40 50 70 50 3065 Barley (winter) 10 10 20 40 20 65 10 60 10 Blackgrass (2) 10 10 20 2020 60 25 20 20 Blk nightshade 80 100 100 100 75 90 100 70 100 Chickweed30 65 60 85 50 70 100 60 70 Common poppy 50 85 100 100 70 100 100 70 100Deadnettle 30 85 100 100 45 100 100 60 80 Downy brome 10 20 20 30 10 7020 10 30 Field violet 100 100 100 100 50 95 100 80 90 Galium (2) 30 8055 60 50 80 85 70 65 Green foxtail 55 70 60 60 15 70 65 30 50 I.Ryegrass 10 10 30 20 5 70 20 20 20 Jointed goatgra 15 20 20 20 10 40 2030 20 Kochia 80 65 65 70 50 70 85 60 70 Lambsquarters 55 100 85 75 30 9590 50 80 LS canarygrass 10 50 65 40 30 70 55 40 65 Rape (1) 70 100 100100 95 90 100 50 85 Redroot pigweed 100 90 75 85 75 95 95 50 80 Russianthistle 55 80 70 75 50 60 75 40 75 Scentless chamo 10 70 60 100 70 95100 30 50 Spring Barley 20 20 20 20 20 60 10 40 10 Sugar beet 100 100100 100 60 95 100 70 100 Sunflower 10 30 30 45 30 60 35 50 20 Veronicahedera 55 98 90 — 80 100 100 70 70 Wheat (spring) 10 20 30 20 10 60 1030 10 Wheat (winter) 10 10 10 20 10 50 10 30 10 Wild buckwheat 40 40 5080 70 50 65 40 45 Wild mustard 100 98 100 80 75 100 100 100 85 Wild oat(1) 10 20 20 30 20 90 20 30 10 Windgrass 10 50 50 30 20 50 50 20 50COMPOUND Rate 125 g/ha 6 12 13 14 16 20 21 22 24 25 29 36 37 49 51 56 57PREEMERGENCE Alfalfa — 100 — — — — — — — — — — — — — — — Annual bluegras75 100 85 70 50 100 60 85 70 80 85 100 100 85 35 100 70 Barley (winter)0 25 30 30 15 20 0 20 15 10 20 10 10 20 5 10 5 Blackgrass (2) 10 75 6040 50 85 50 40 50 55 50 70 60 50 15 30 20 Blk nightshade 10 100 100 10040 100 10 40 65 85 100 90 100 100 30 100 80 Chickweed 50 85 85 70 75 7530 100 75 85 100 100 100 85 20 100 65 Common poppy — — 100 100 100 100100 100 100 100 100 100 100 100 60 100 100 Deadnettle 85 85 70 70 70 85— 75 70 70 75 70 90 100 40 — — Downy brome 10 100 50 60 40 80 10 30 5565 10 100 100 50 0 10 20 Field violet 80 85 85 85 70 100 10 85 85 85 8565 100 100 85 100 60 Galium (2) 30 100 100 100 100 100 30 70 100 100 100100 100 — 70 100 100 Green foxtail 60 100 100 75 100 100 60 100 100 100100 100 100 100 80 100 95 I. Ryegrass 20 100 50 50 50 75 45 15 20 30 30100 70 30 10 20 10 Jointed goatgra 10 55 30 45 30 60 0 15 30 30 10 50 3520 10 30 5 Kochia 85 — 85 75 65 75 5 60 90 70 70 100 100 70 60 70 100Lambsquarters 10 70 85 70 75 75 50 85 70 70 70 75 70 70 70 70 70 Lentil— 60 — — — — — — — — — — — — — — — LS canarygrass 10 100 65 85 40 100 6065 40 60 100 75 100 85 20 100 60 Pea — 20 — — — — — — — — — — — — — — —Potato — 0 — — — — — — — — — — — — — — — Rape (1) 10 85 90 85 70 85 1060 65 85 85 85 85 100 20 100 90 Redroot pigweed 85 100 85 85 75 100 50100 70 70 70 70 70 85 70 70 75 Russian thistle 0 100 50 50 40 80 0 20 6065 60 100 100 100 10 100 50 Scentless chamo 55 — — — 100 100 — — 70 7070 70 70 85 — 75 70 Sorghum — 30 — — — — — — — — — — — — — — — SpringBarley 0 20 20 50 20 10 0 20 10 10 10 10 10 20 10 10 5 Sugar beet — 100100 85 100 100 40 100 100 100 100 100 100 100 60 85 75 Sunflower 0 30 2020 20 25 0 20 30 60 50 50 60 15 10 10 10 Veronica hedera 60 100 100 100100 100 60 100 100 100 100 100 100 — 100 — — Wheat (spring) 10 25 20 3020 10 0 10 10 10 2 30 30 20 5 20 5 Wheat (winter) 0 20 20 40 10 10 0 2010 0 2 20 10 10 10 10 2 Wild buckwheat 10 75 100 85 55 80 40 60 60 85 8595 100 100 30 85 85 Wild mustard 50 100 100 100 100 100 80 85 100 100100 100 100 100 100 85 85 Wild oat (1) 10 75 50 50 55 85 30 60 60 50 4545 50 50 10 10 20 Windgrass 50 100 100 100 100 100 70 85 100 100 85 100100 100 70 75 75 COMPOUND Rate 62 g/ha 12 13 14 20 21 22 49 50 51 52 5657 POSTEMERGENCE Annual bluegras 30 20 30 20 20 50 30 50 20 50 60 60Barley (winter) 10 10 10 30 30 60 10 40 50 50 10 10 Blackgrass (2) 10 1010 20 10 40 20 30 20 40 20 20 Blk nightshade 100 85 100 100 75 90 100 6090 80 100 90 Chickweed 55 60 60 70 30 75 70 30 40 60 60 50 Common poppy100 60 100 85 40 100 100 70 30 80 100 50 Deadnettle 100 85 80 85 30 100100 70 60 70 80 65 Downy brome 10 10 20 15 5 30 10 0 10 30 10 10 Fieldviolet 100 100 100 100 30 90 100 90 30 70 100 80 Galium (2) 65 50 50 5520 70 65 30 50 70 60 55 Green foxtail 65 50 40 60 10 50 50 20 20 60 6550 I. Ryegrass 10 10 10 10 2 20 15 20 20 20 10 5 Jointed goatgra 10 1010 10 5 40 10 20 20 30 10 10 Kochia 70 60 55 65 30 70 75 70 60 60 70 85Lambsquarters 85 100 80 85 30 90 90 80 50 80 80 65 LS canarygrass 20 2030 30 20 60 30 40 30 40 60 25 Rape (1) 100 85 80 100 100 80 95 60 50 50100 80 Redroot pigweed 85 65 60 80 70 95 90 90 50 95 70 80 Russianthistle 70 70 60 75 30 50 75 30 40 40 70 65 Scentless chamo 55 — 30 6550 80 60 80 30 30 30 30 Spring Barley 10 10 10 10 10 50 10 40 30 40 1010 Sugar beet 100 90 100 100 50 90 100 80 50 80 100 80 Sunflower 20 2020 50 30 60 30 70 40 50 10 40 Veronica hedera 100 98 100 — 75 100 100100 80 95 75 60 Wheat (spring) 10 10 20 10 10 50 10 30 30 30 10 15 Wheat(winter) 10 10 10 10 10 40 10 30 20 30 10 10 Wild buckwheat 40 40 30 8045 50 40 30 40 50 60 50 Wild mustard 100 80 100 70 75 100 100 60 100 90100 95 Wild oat (1) 20 10 10 20 20 70 15 20 30 50 10 10 Windgrass 20 2020 30 10 30 30 20 20 30 30 30 COMPOUND Rate 62 g/ha 12 13 14 20 21 22 2425 29 36 37 49 50 51 52 56 57 PREEMERGENCE Alfalfa 100 — — — — — — — — —— — — — — Annual bluegras 100 75 70 85 20 100 60 60 55 70 70 80 50 85 2075 70 Barley (winter) 10 35 20 10 0 10 5 10 30 10 10 10 30 0 10 5 10Blackgrass (2) 50 15 55 20 40 20 50 30 30 55 60 20 30 10 20 10 10 Blknightshade 65 85 65 60 0 30 60 50 85 60 100 100 0 20 10 100 60 Chickweed80 85 85 85 15 50 75 85 75 100 85 80 30 20 70 80 60 Common poppy — 100100 100 70 70 100 100 100 100 100 100 90 — 60 100 100 Deadnettle 75 7085 100 — 85 60 55 70 85 85 100 100 30 10 — — Downy brome 65 30 50 55 2020 30 50 40 85 50 25 50 5 5 20 5 Field violet 100 100 85 100 0 100 70 6570 65 60 85 50 65 60 100 60 Galium (2) 100 100 100 100 0 60 100 100 100100 100 — 40 — 40 100 100 Green foxtail 100 100 60 100 50 100 85 100 100100 100 100 80 35 100 100 10 I. Ryegrass 10 30 30 50 10 10 20 30 20 8565 55 0 10 10 10 5 Jointed goatgra 20 20 10 — 5 — 30 30 10 30 35 10 20 010 5 0 Kochia — 70 40 70 5 50 55 100 65 100 100 60 30 30 60 60 50Lambsquarters 70 65 65 70 30 65 70 70 70 70 70 70 80 60 85 100 70 Lentil30 — — — — — — — — — — — — — — — — LS canarygrass 100 20 60 75 20 45 3050 20 65 60 85 40 40 30 30 50 Pea 10 — — — — — — — — — — — — — — — —Potato 0 — — — — — — — — — — — — — — — — Rape (1) 80 100 65 80 10 55 6575 80 85 85 85 30 10 40 100 100 Redroot pigweed 100 100 85 70 0 85 70 7070 70 — 100 90 — 100 100 70 Russian thistle 100 20 20 60 0 10 30 30 70100 50 35 20 5 0 50 30 Scentless chamo 70 — — 80 — — 70 70 70 70 70 6090 — — 70 70 Sorghum 10 — — — — — — — — — — — — — — — — Spring Barley 2010 10 10 0 10 5 10 10 5 10 20 0 5 5 10 2 Sugar beet 100 100 85 100 50 50100 100 85 100 100 100 30 55 60 30 85 Sunflower 50 20 10 15 10 10 20 5550 35 60 20 30 5 10 5 0 Veronica hedera 100 100 100 100 50 70 100 100100 100 100 — — 100 100 — — Wheat (spring) 10 10 10 5 10 10 5 2 2 10 2020 30 0 0 10 5 Wheat (winter) 10 20 30 10 5 10 5 0 5 20 20 10 10 0 5 5 0Wild buckwheat 30 85 60 70 5 25 60 80 65 80 75 80 30 50 50 30 50 Wildmustard 100 100 70 100 55 80 85 100 85 100 100 100 80 60 70 85 70 Wildoat (1) 30 40 20 30 10 30 30 20 30 30 50 80 50 0 20 10 10 Windgrass 10085 100 85 15 50 100 100 100 100 100 100 70 60 70 70 55 COMPOUND Rate 31g/ha 13 14 20 21 22 49 50 51 52 56 57 POSTEMERGENCE Annual bluegras 1020 15 20 30 20 50 10 30 50 50 Barley (winter) 10 10 20 10 60 10 40 50 5010 10 Blackgrass (2) 10 10 10 10 20 10 30 10 30 10 10 Blk nightshade 10075 100 70 90 100 60 70 90 75 80 Chickweed 50 50 55 45 70 60 10 40 60 6050 Common poppy 50 85 85 30 100 100 50 20 60 85 50 Deadnettle 85 60 8030 70 85 60 60 40 75 60 Downy brome 10 20 10 2 30 10 0 10 20 10 5 Fieldviolet 100 100 100 10 80 100 60 30 50 70 70 Galium (2) 40 40 50 20 50 7040 30 50 60 50 Green foxtail 30 10 30 10 30 10 0 20 30 30 60 I. Ryegrass10 10 10 0 20 10 0 20 20 10 5 Jointed goatgra 10 10 10 2 30 10 20 20 3010 10 Kochia 50 50 60 20 60 75 50 60 60 60 60 Lambsquarters 100 85 80 070 100 50 30 70 75 65 LS canarygrass 10 20 20 10 40 10 40 20 30 55 20Rape (1) 85 55 100 60 60 75 60 20 50 70 65 Redroot pigweed 55 50 70 6090 85 50 20 80 70 70 Russian thistle 60 50 70 20 40 60 20 20 30 60 70Scentless chamo 30 20 70 0 70 50 80 20 20 10 10 Spring Barley 10 10 15 540 10 50 30 40 10 10 Sugar beet 65 55 100 30 60 75 100 40 70 98 98Sunflower 15 20 30 30 30 20 50 20 30 20 30 Veronica hedera 100 98 — 70100 100 50 70 90 70 55 Wheat (spring) 10 10 10 5 40 10 20 10 20 10 10Wheat (winter) 10 10 10 5 30 10 30 10 30 10 5 Wild buckwheat 30 20 30 3050 40 45 20 50 40 55 Wild mustard 60 70 100 60 100 95 40 70 90 90 95Wild oat (1) 10 10 10 30 60 10 0 20 40 20 10 Windgrass 10 10 20 10 30 2020 10 20 20 20 COMPOUND Rate 31 g/ha 12 13 14 16 20 21 22 24 36 37 49 5051 52 56 PREEMERGENCE Alfalfa 60 — — — — — — — — — — — — — Annualbluegras 100 55 60 30 60 10 50 50 50 60 75 40 10 10 40 Barley (winter)10 10 10 5 5 10 5 5 10 0 20 0 0 5 2 Blackgrass (2) 30 10 10 20 10 30 1030 20 50 10 30 5 10 10 Blk nightshade 35 60 50 20 50 0 20 50 60 50 60 010 5 60 Chickweed 75 85 70 70 60 10 20 70 85 70 85 0 30 30 85 Commonpoppy — 85 100 100 100 65 60 100 100 100 100 90 25 20 100 Deadnettle 3070 60 60 85 — 30 70 55 65 85 50 20 5 — Downy brome 20 40 30 15 10 10 1020 50 50 10 50 0 0 0 Field violet 50 70 70 70 70 50 50 60 10 50 60 30 7065 30 Galium (2) 100 100 70 70 100 0 50 60 100 60 — 0 10 20 100 Greenfoxtail 100 55 50 100 100 30 50 100 100 100 100 40 10 55 60 I. Ryegrass20 20 45 10 20 20 10 20 10 30 10 0 0 5 20 Jointed goatgra 10 10 20 10 100 0 10 20 20 5 20 0 5 10 Kochia — 65 30 60 60 0 30 50 100 100 55 20 1050 50 Lambsquarters 65 70 65 70 55 60 30 70 60 65 70 30 50 100 100Lentil 20 — — — — — — — — — — — — — — LS canarygrass 100 20 30 20 20 1015 20 — 60 75 50 5 20 20 Pea 10 — — — — — — — — — — — — — — Potato 10 —— — — — — — — — — — — — — Rape (1) 65 50 10 60 50 0 30 60 60 100 65 0 1020 100 Redroot pigweed 80 70 85 70 75 30 60 70 — 65 100 90 50 65 100Russian thistle 100 30 10 20 30 5 0 20 20 30 20 0 0 0 10 Scentless chamo— — — 70 70 — — 100 60 70 70 50 — — 10 Sorghum 5 — — — — — — — — — — — —— — Spring Barley 10 10 10 2 5 0 10 2 10 10 10 0 2 5 5 Sugar beet 100 8570 60 65 30 35 90 100 100 100 30 10 50 45 Sunflower 20 0 10 40 10 10 0 025 55 10 30 0 5 5 Veronica hedera 100 100 100 70 100 50 100 100 100 100— — 65 100 — Wheat (spring) 5 5 20 10 0 0 5 2 10 10 10 10 0 0 10 Wheat(winter) 5 5 20 0 5 0 5 2 10 0 0 0 10 0 0 Wild buckwheat 20 65 55 30 600 10 35 60 65 50 30 20 10 40 Wild mustard 100 85 65 100 85 40 60 70 100100 100 60 50 55 100 Wild oat (1) 20 20 30 20 10 20 10 20 20 20 30 50 010 10 Windgrass 100 50 100 100 55 50 45 80 100 100 100 50 30 60 50COMPOUND COMPOUND Rate 16 g/ha 52 Rate 16 g/ha 12 52 56 57 POSTEMERGENCEPREEMERGENCE Annual bluegras 20 Alfalfa 50 — — — Barley (winter) 40Annual bluegras 30 5 20 10 Blackgrass (2) 20 Barley (winter) 5 0 5 10Blk nightshade 90 Blackgrass (2) 50 5 5 0 Chickweed 60 Blk nightshade 302 30 35 Common poppy 40 Chickweed 10 0 75 50 Deadnettle 20 Common poppy— 65 60 100 Downy brome 10 Deadnettle 20 0 65 30 Field violet 30 Downybrome 10 10 5 5 Galium (2) 20 Field violet 20 10 5 0 Green foxtail 30Galium (2) 60 10 40 30 I. Ryegrass 0 Green foxtai1 60 50 60 30 Jointedgoatgra 20 I. Ryegrass 10 0 5 5 Kochia 50 Jointed goatgra 5 0 10 0Lambsquarters 30 Kochia — 30 50 10 LS canarygrass 30 Lambsquarters 15 3070 65 Rape (1) 30 Lentil 10 — — — Redroot pigweed 30 LS canarygrass 10 520 5 Russian thistle 10 Pea 5 — — — Scentless chamo 0 Potato 0 — — —Spring Barley 30 Rape (1) 55 10 85 65 Sugar beet 50 Redroot pigweed 7055 70 40 Sunflower 20 Russian thistle 85 0 50 10 Veronica hedera 80Scentless chamo — — 0 20 Wheat (spring) 10 Sorghum 5 — — — Wheat(winter) 30 Spring Barley 5 0 10 0 Wild buckwheat 60 Sugar beet 100 1040 65 Wild mustard 70 Sunflower 10 0 10 10 Wild oat (1) 30 Veronicahedera 100 100 100 100 Windgrass 10 Wheat (spring) 5 0 0 0 Wheat(winter) 0 0 0 0 Wild buckwheat 10 0 30 20 Wild mustard 100 45 100 50Wild oat (1) 10 15 5 0 Windgrass 101 45 10 10 COMPOUND COMPOUND COMPOUNDRate 8 g/ha 12 Rate 4 g/ha 12 Rate 2 g/ha 12 PREEMERGENCE PREEMERGENCEPREEMERGENCE Alfalfa 50 Alfalfa 20 Alfalfa 30 Annual bluegras — Annualbluegras — Annual bluegras — Barley (winter) 5 Barley (winter) 0 Barley(winter) 0 Blackgrass (2) — Blackgrass (2) — Blackgrass (2) — Blknightshade — Blk nightshade — Blk nightshade — Chickweed — Chickweed —Chickweed — Common poppy — Common poppy — Common poppy — Deadnettle —Deadnettle — Deadnettle — Downy brome — Downy brome — Downy brome —Field violet — Field violet — Field violet — Galium (2) — Galium (2) —Galium (2) — Green foxtail — Green foxtail — Green foxtail — I. Ryegrass— I. Ryegrass — I. Ryegrass — Jointed goatgra — Jointed goatgra —Jointed goatgra — Kochia — Kochia — Kochia — Lambsquarters —Lambsquarters — Lambsquarters — Lentil 5 Lentil 0 Lentil 0 LScanarygrass — LS canarygrass — LS canarygrass — Pea 5 Pea 10 Pea 0Potato 0 Potato 0 Potato 0 Rape (1) 10 Rape (1) 20 Rape (1) 10 Redrootpigweed — Redroot pigweed — Redroot pigweed — Russian thistle — Russianthistie — Russian thistle — Scentless chamo — Scentiess chamo —Scentless chamo — Sorghum 2 Sorghum 0 Sorghum 0 Sprlng Barley 5 SpringBarley 0 Spring Barley 0 Sugar beet 10 Sugar beet 15 Sugar beet 0Sunflower 0 Sunflower 0 Sunflower 0 Veronica hedera — Veronica hedera —Veronica hedera — Wheat (sprlng) 0 Wheat (spring) 0 Wheat (spring) 0Wheat (winter) 0 Wheat (winter) 0 Wheat (winter) 0 Wild buckwheat — Wildbuckwheat — Wild buckwheat — Wild mustard — Wild mustard — Wild mustard— Wild oat (1) — Wild oat (1) — Wild oat (1) — Windgrass — Windgrass —Windgrass — COMPOUND Lentil 0 Rate 1 g/ha 12 LS canarygrass —PREEMERGENCE Pea 0 Alfalfa 5 Potato 0 Annual bluegras — Rape (1) 0Barley (winter) 0 Redroot pigweed — Blackgrass (2) — Russian thistle —Blk nightshade — Scentless chamo — Chickweed — Sorghum 0 Common poppy —Spring Barley 0 Deadnettle — Sugar beet 0 Downy brome — Sunflower 0Field violet — Veronica hedera — Galium (2) — Wheat (spring) 0 Greenfoxtail — Wheat (winter) 0 I. Ryegrass — Wild buckwheat — Jointedgoatgra — Wild mustard — Kochia — Wild oat (1) — Lambsquarters —Windgrass —

What is claimed is:
 1. A compound selected from Formula I, geometric orstereoisomers thereof, N-oxides thereof, and agriculturally suitablesalts thereof,

W is N or CR⁹; X, Y and Z are independently N, CH or CR⁹, provided thatonly one of X, Y and Z is CR⁹; Q is O or S(O)_(n); R¹ and R² areindependently H, halogen, cyano, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₂-C₄alkoxyalkyl, C₃-C₅ dialkoxyalkyl, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄alkoxyalkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄ alkenyloxy, C₃-C₄alkynyloxy, S(O)_(n)R⁸, C₂-C₄ alkylthioalkyl, C₂-C₄ alkylsulfonylalkyl,C₁-C₄ alkylamino or C₂-C₄ dialkylamino; R³ is C₁-C₄ haloalkyl; R⁴ ishalogen, cyano, SF₅, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy orS(O)_(n)R⁸; R⁵ is H, halogen, cyano, SF₅, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy or S(O)_(n)R⁸; R⁶ is H, halogen, cyano, SF₅, C₁-C₄haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or S(O)_(n)R⁸; R⁷ is halogen,cyano, SF₅, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy orS(O)_(n)R⁸; each R⁸ is independently C₁-C₄ alkyl or C₁-C₄ haloalkyl;each R⁹ is independently halogen, cyano, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkoxyalkyl, C₃-C₄ alkenyl, C₃-C₄alkynyl, C₃-C₄ alkenyloxy, C₃-C₄ alkynyloxy or S(O)_(n)R⁸; R¹⁰ is H,C₁-C₄ alkyl or C₁-C₄ haloalkyl; and each n is independently 0, 1 or 2.2. A compound of claim 1 wherein: Q is O; R¹ and R² are independently H,C₁-C₄ alkyl or C₁-C₄ alkoxy.
 3. A compound of claim 2 wherein: W is N; Yis CR⁹; and R⁵ is H.
 4. A compound of claim 3 wherein: R² is H; and eachR⁴ is independently halogen, C₁-C₄ haloalkyl, C₁-C₄ haloalkoxy or C₁-C₄haloalkylthio.
 5. The compound of claim 4 which is selected from thegroup: (a)5-methyl4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;(b)4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;(c)5-methyl-4-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]pyrimidine;(d)5-methyl-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-4-[[6-(trifluoromethyl)-2-pyridinyl]oxy]pyrimidine;(e) 5-methyl-4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]pyrimidine; (f)5-methyl-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]-4-[3-(trifluoromethyl)phenoxy]pyrimidine;(g)5-ethyl-4-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;(h)5-ethyl-4-[3-(trifluoromethoxy)phenoxy]-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine;(i)5-ethyl-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]-4-[3-(trifluoromethyl)phenoxy]pyrimidine;and (j)5-ethyl-4-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]pyrimidine.6. A compound selected from Formula 1a and agriculturally suitable saltsthereof,

wherein X, Y and Z are independently N, CH or CR⁹, provided that onlyone of X, Y and Z is CR⁹; R¹ is H, C₁-C₄ alkyl or C₁-C₄ alkoxy; R³ isC₁-C₄ haloalkyl; each R⁹ is independently halogen or cyano; and n is 0,1 or2.
 7. A compound of claim 6 wherein R¹ is C₁-C₄ alkyl.
 8. Aherbicidal composition comprising a herbicidally effective amount of acompound of claim 1 and at least one of a surfactant, a solid diluent ora liquid diluent.
 9. A method for controlling the growth of undesiredvegetation comprising contacting the vegetation or its environment witha herbicidally effective amount of a compound of claim 1.